(S)-4,4-difluoro-2-(5-hydroxy-adamantan-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester → (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide

HRID 1644805Notes

Reaction equation

HRID 1644805 reaction equation
C(OC([N:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:12]1[C:18](=[O:31])[NH:19][CH:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][C:25]([OH:30])([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2)=O)C1C=CC=CC=1>C(O)C.[Pd]>[OH:30][C:25]12[CH2:29][CH:21]3[CH2:22][CH:23]([CH2:28][CH:27]([CH:20]3[NH:19][C:18]([C@@H:12]3[CH2:13][C:14]([F:17])([F:16])[CH2:15][NH:11]3)=[O:31])[CH2:26]1)[CH2:24]2

Participants

4

Reactant 1

HCID 66773599(S)-4,4-difluoro-2-(5-hydroxy-adamantan-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 66773511(S)-4,4-difluoro-pyrrolidine-2-carboxylic acid (5-hydroxy-adamantan-2-yl)-amideYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd—C (10%, 0.5 g) was added to a solution of (S)-4,4-difluoro-2-(5-hydroxy-adamantan-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (1.2 g) in ethanol (50 mL) and the reaction mixture was hydrogenated (1 atm pressure) under stirring condition for 10 h. Reaction was monitored by TLC. After completion, reaction mixture was filtrated through Celite®. The filtrate was concentrated under reduced pressure using a rotary evaporator to give 0.8 g (93%) of the desired (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide.

Workup

  1. customReaction
  2. customAfter completion, reaction mixture
  3. filtrationwas filtrated through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-4be12d34664d4f28bd8c545261e91896
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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