Dimethyl Sulfoxide → tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

HRID 383121

반응식

HRID 383121 반응식
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:18]([N:25]1[CH2:29][C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][C@H:26]1[CH2:38][OH:39])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C>ClCCl>[C:18]([N:25]1[CH2:29][C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][C@H:26]1[CH:38]=[O:39])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 1 ml (14.1 mmol) of DMSO in 7 ml of dichloromethane were added 1.48 ml (10.4 mmol) of trifluoroacetic anhydride in 3.5 ml of dichloromethane at −78° C. under a slight stream of argon. After 10 min, 2.35 g (7 mmol) of (2S,4R)-1-Boc-4-[t-butyldimethylsilyloxy]-2-(hydroxymethyl)pyrrolidine, prepared as in Example 171A, in 7 ml of dichloromethane was added to this mixture at the same temperature. The reaction mixture was stirred for 1 hour. To this solution was added 3 ml (21.5 mmol) of triethylamine. The reaction mixture was stirred for 1 hour at −78° C., slowly warmed to room temperature, and concentrated. The residue was chromatographed on silica gel (9:1 hexanes-ethyl acetate to yield 1.08 g (47%) of (2S,4R)-1-Boc-4-[t-butyldimethylsilyloxy]-pyrrolidin-2-aldehyde as an oil:

후처리

  1. stirringThe reaction mixture was stirred for 1 hour at −78° C.
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel (9:1 hexanes-ethyl acetate

출처 및 근거

ORD 기록
ord-77092eb13352433bae14428df84b8526
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310095B1

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