pv

Query 1. Query

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Date

RX.PXRN=1346797

9 reactions in Reaxys

2018-07-07 12h:46m:30s (UTC)

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2018-07-07 13:05:01

OH H N

O

N

Rx-ID: 39395167 View in Reaxys 1/9 Yield

Conditions & References Stage 1: With N-Bromosuccinimide in 1,4-dioxane Stage 2: in 1,4-dioxane, Time= 24h, T= 20 °C Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys

O

O

Cl

H N

N

Rx-ID: 28001414 View in Reaxys 2/9 Yield

Conditions & References 5; 39 :Example 5 l-Phenyl-3-pyrrolidin-1-yl-2 p-tolyl-hexan-2-ol, hydrogen chloride salt. The pyrovalerone (2.0 g, 7.1 mmol) was freed from its HCI salt by treatment with 20percent Na2C03 and extraction'of the organics into Et20. The Et20 extracts were dried (MgS04), filtered and reduced in vacuo to a pale yellow oil. This oil was taken up in toluene (20 mL) and cooled on an ice bath. Benzylmagnesium chloride (3.9 mL, 2.0 M solution in THF, 7.8 mmol, 1.1 mol eq. ) was added via syringe over 5 min to the solution which was subsequently hydrolyzed by addition of 1 M HCI (20 mL). The resulting flocculent white precipitate was collected by filtration, washed with 1 M HCI (5 mL), then Et20 (50 mL), dried under suction, then in air. Recrystallization from EtOH/Et2O afforded pure 1-phenyl-3-pyrrolidin-1-yl-2-p-tolyl-hexan-2-ol, as its hydrogen chloride salt (2.0 g, 75percent) : Mp 211 °C (dec. ) ;'H NMR 6 9.5-9. 3 (br, 1H), 7.41 (d, 2H), 7.2-7. 0 (m, 7H), 6.07 (s, 1H), 3.

85-3. 6 (br, m, 2H), 3.41 (m, 2H), 3.15-2. 9 (m, 2H), 3. 8-3. 6 (m, 1H), 2.25 (s, 3H), 1.95-1. 75 (br, m, 5H), 1.4-1. 1 (m, 2H), 1.1-0. 9 (m, 1H), 0.78 (t, 311); 13C NNM 8 137.7, 136.4, 136.2, 130.8, 128.3, 127.3, 126.7, 125.8, 77.6, 72.0, 55.9, 44.0, 26.3, 24.4, 22.6, 22.2, 20.6, 14.0 ; APCI MS m/z 338 (M + 1); Anal. (C23H32ClNO) C, H, N, Cl. With sodium carbonate in water, pH= 8 - 9 Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; ORGANIX, INC.; WO2005/34878; (2005); (A2) English View in Reaxys

O H N

O

Br N

Rx-ID: 10159147 View in Reaxys 3/9 Yield

Conditions & References in water, Time= 24h, T= 20 °C Xu, Senhan; Wu, Ping; Zhang, Wei; Organic and Biomolecular Chemistry; vol. 14; nb. 48; (2016); p. 11389 - 11395 View in Reaxys

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2018-07-07 13:05:01

in diethyl ether Meltzer, Peter C.; Butler, David; Deschamps, Jeffrey R.; Madras, Bertha K.; Journal of Medicinal Chemistry; vol. 49; nb. 4; (2006); p. 1420 - 1432 View in Reaxys

O O

N

Rx-ID: 12456807 View in Reaxys 4/9 Yield

Conditions & References Reaction Steps: 2 1: AlCl3; bromine 2: diethyl ether With aluminium trichloride, bromine in diethyl ether Meltzer, Peter C.; Butler, David; Deschamps, Jeffrey R.; Madras, Bertha K.; Journal of Medicinal Chemistry; vol. 49; nb. 4; (2006); p. 1420 - 1432 View in Reaxys

O

Cl

O

N

Rx-ID: 12463796 View in Reaxys 5/9 Yield

Conditions & References Reaction Steps: 3 1: AlCl3; bromine 2: diethyl ether With aluminium trichloride, bromine in diethyl ether, 1: Friedel-Crafts acylation Meltzer, Peter C.; Butler, David; Deschamps, Jeffrey R.; Madras, Bertha K.; Journal of Medicinal Chemistry; vol. 49; nb. 4; (2006); p. 1420 - 1432 View in Reaxys

O

iron-powder N

Rx-ID: 12466152 View in Reaxys 6/9 Yield

Conditions & References Reaction Steps: 3 1: AlCl3; bromine 2: diethyl ether With aluminium trichloride, bromine in diethyl ether, 1: Friedel-Crafts acylation

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3/5

2018-07-07 13:05:01

Meltzer, Peter C.; Butler, David; Deschamps, Jeffrey R.; Madras, Bertha K.; Journal of Medicinal Chemistry; vol. 49; nb. 4; (2006); p. 1420 - 1432 View in Reaxys

O O

N

Rx-ID: 39395143 View in Reaxys 7/9 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: N-Bromosuccinimide / 1,4-dioxane 2.2: 24 h / 20 °C With N-Bromosuccinimide, iodine, magnesium in tetrahydrofuran, 1,4-dioxane, 1.1: |Grignard Reaction Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys

O

Br

N

Rx-ID: 39395201 View in Reaxys 8/9 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: N-Bromosuccinimide / 1,4-dioxane 2.2: 24 h / 20 °C With N-Bromosuccinimide, iodine, magnesium in tetrahydrofuran, 1,4-dioxane, 1.1: |Grignard Reaction Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys

O

N

Rx-ID: 44135499 View in Reaxys 9/9 Yield

Conditions & References Reaction Steps: 2 1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water / 2 h / 60 °C / Green chemistry 2: water / 24 h / 20 °C

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

4/5

2018-07-07 13:05:01

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, water in water Xu, Senhan; Wu, Ping; Zhang, Wei; Organic and Biomolecular Chemistry; vol. 14; nb. 48; (2016); p. 11389 - 11395 View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

5/5

2018-07-07 13:05:01