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

HRID 1245623노트

반응식

HRID 1245623 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)-phenylpyrrolidine

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 tert-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 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-54e290a35dc54874827f6db142a6a2bd
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125887B2

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