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

HRID 1917283ノート

反応式

HRID 1917283 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f893a2356254c838d6c87a68aa8277d
出典データセット
uspto-grants-2013_12
特許番号
US08618094B2

反応ノート

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