tert-Butyldimethylsilyl chloride → 1-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine

HRID 1068099노트

반응식

HRID 1068099 반응식
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][O:20][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

생성물 1

HCID 213410481-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 82.0 g (0.31 mol) of 1-benzyl-3-(R)-hydroxymethyl-4-(S)-phenyl pyrrolidine (from Step C) and 46.5 g (0.36 mol) of N,N-diisopropylethylamine in 1 L of CH2Cl2 was treated with 54.2 g (0.36 mol) of t-butyldimethylsilyl chloride and the resulting mixture was stirred at rt for 20 h. The reaction was quenched with 750 mL of sat'd NaHCO3 and the layers were separated. The organic layer was combined with 150 g of silica gel and aged for 45 min. The mixture was filtered and the filtrate was concentrated to afford 117 g (100%) of the title compound.

후처리

  1. customThe reaction was quenched with 750 mL of sat'd NaHCO3
  2. customthe layers were separated
  3. waitThe organic layer was combined with 150 g of silica gel and aged for 45 min
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-d87bd8090e1d4e8882fb6b7a575a3b3e
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248755B1

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