(±)-threo-4-Fluoromethylphenidate (4-FTMP)

Page 1

Query Query

O

1. Query

Results

Date

6 reactions in Reaxys

2017-08-24 00h:29m:49s (EST)

O

H N

F racemate

Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals AND (IDE.XRN=7517152)

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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N

O

Br

O

H N

F racemate

Rx-ID: 17747654 View in Reaxys 1/6 Yield

Conditions & References Reaction Steps: 5 1: 1.) t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, a) RT, 1 h, b) reflux, overnight 2: 12 N HCl / 15 h / Ambient temperature 3: H2 / 5percent Pt/C / acetic acid / 10 h / 1551.4 - 2068.6 Torr 4: 1.) 6N HCl, 2.) 50percent KOH / 1.) reflux, 6 h, 2.) reflux, 4 d 5: SOCl2 / 24 h / Ambient temperature With hydrogenchloride, potassium hydroxide, thionyl chloride, potassium tert-butylate, hydrogen, platinum on activated charcoal in acetic acid Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys

O

O

H N

N F

F racemate

Rx-ID: 17753084 View in Reaxys 2/6 Yield

Conditions & References Reaction Steps: 5 1: 1.) t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, a) RT, 1 h, b) reflux, overnight 2: 12 N HCl / 15 h / Ambient temperature 3: H2 / 5percent Pt/C / acetic acid / 10 h / 1551.4 - 2068.6 Torr 4: 1.) 6N HCl, 2.) 50percent KOH / 1.) reflux, 6 h, 2.) reflux, 4 d 5: SOCl2 / 24 h / Ambient temperature With hydrogenchloride, potassium hydroxide, thionyl chloride, potassium tert-butylate, hydrogen, platinum on activated charcoal in acetic acid Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys

N

O

O

H N

N

F

F

racemate

Rx-ID: 17761480 View in Reaxys 3/6 Yield

Conditions & References Reaction Steps: 4 1: 12 N HCl / 15 h / Ambient temperature 2: H2 / 5percent Pt/C / acetic acid / 10 h / 1551.4 - 2068.6 Torr 3: 1.) 6N HCl, 2.) 50percent KOH / 1.) reflux, 6 h, 2.) reflux, 4 d 4: SOCl2 / 24 h / Ambient temperature With hydrogenchloride, potassium hydroxide, thionyl chloride, hydrogen, platinum on activated charcoal in acetic acid Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys

O

NH 2

O

O

H N

N

F

F racemate

Rx-ID: 17773109 View in Reaxys 4/6 Yield

Conditions & References Reaction Steps: 3 1: H2 / 5percent Pt/C / acetic acid / 10 h / 1551.4 - 2068.6 Torr 2: 1.) 6N HCl, 2.) 50percent KOH / 1.) reflux, 6 h, 2.) reflux, 4 d 3: SOCl2 / 24 h / Ambient temperature With hydrogenchloride, potassium hydroxide, thionyl chloride, hydrogen, platinum on activated charcoal in acetic acid Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys

O

NH 2

O

H N

O

H N F

F racemate

Rx-ID: 17774872 View in Reaxys 5/6 Yield

Conditions & References Reaction Steps: 2 1: 1.) 6N HCl, 2.) 50percent KOH / 1.) reflux, 6 h, 2.) reflux, 4 d 2: SOCl2 / 24 h / Ambient temperature With hydrogenchloride, potassium hydroxide, thionyl chloride Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys

HO

HO

O

O

H N

O

O

O

H N

H N F

F

F

racemate

racemate

Rx-ID: 4462120 View in Reaxys 6/6 Yield

Conditions & References With thionyl chloride, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys With thionyl chloride, Time= 24h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Deutsch, Howard M.; Shi, Qing; Gruszecka-Kowalik, Ewa; Schwer, Margaret M.; Journal of Medicinal Chemistry; vol. 39; nb. 6; (1996); p. 1201 - 1209 View in Reaxys

Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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