Triethylamine → (3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917301ノート

反応式

HRID 1917301 の反応式
C(N(CC)CC)C.[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][OH:31])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].FC(F)(F)S(O[Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][O:31][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 67491029HCID 67491029、化合物

生成物 1

HCID 67490763(3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester収率 88%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (3.0 mL, 21.8 mmol) was added to a solution of (3S)-3-(2-hydroxyethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.42 g, 7.25 mmol) in dichloromethane (70 mL), and the mixture was cooled to 0° C. tert-Butyldimethylsilyl trifluoromethanesulfonate (2.50 mL, 10.9 mmol) was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After addition of an ice piece and stirring, the reaction solution was poured into a mixture of ethyl acetate (50 mL) and saturated sodium bicarbonate (50 mL), followed by extraction with ethyl acetate (200 mL, 100 mL). The organic layers were combined and washed with brine (50 mL). After drying over anhydrous sodium sulfate and filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1) to give 2.84 g (88%) of the title compound as a white solid.

後処理

  1. additionwas added dropwise
  2. stirringstirring
  3. extractionfollowed by extraction with ethyl acetate (200 mL, 100 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1)

出典と根拠

ORDレコード
ord-af69ea3039714f8e9d8b70f371f870bb
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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