Pyridine, hydrofluoride (1:1) → 4-[(R)-2-Hydroxy-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 1917283Notes

Reaction equation

HRID 1917283 reaction equation
N1C=CC=CC=1.F.[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@@H:17]([CH3:27])[CH2:18][O:19][Si](C(C)(C)C)(C)C)[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]>N1C=CC=CC=1>[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@@H:17]([CH3:27])[CH2:18][OH:19])[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 674907934-[(R)-2-(tert-Butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

Product 1

HCID 674908004-[(R)-2-Hydroxy-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl esterYield 179.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen fluoride-pyridine (4 mL) was added to a solution of 4-[(R)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (6.0 g, 7.1 mmol) in pyridine (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 13 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate and washing with 1N hydrochloric acid and brine. After drying over magnesium sulfate and filtration, the solvent was evaporated under reduced pressure to give 4.1 g (93%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with 1N hydrochloric acid and brine
  4. dry with materialAfter drying over magnesium sulfate and filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1f893a2356254c838d6c87a68aa8277d
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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