Water → tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 45582

반응식

HRID 45582 반응식
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[S:21]([O:11][CH2:10][C@@H:9]1[CH2:12][CH2:13][CH2:14][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

참가 물질

7

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 643448(S)-(-)-N-Boc-prolinol

생성물 1

HCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate수율 99%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A solution of N-Boc-L-prolinol (51.2 g, 254 mmol) in dichloromethane (250 mL) was cooled to 0° C., and thereto were added p-toluenesulfonylchloride (53.4 g, 280 mmol), triethylamine (30.9 g, 42.6 mL, 305 mmol), and 4-dimethylaminopyridine (5.00 g, 40.9 mmol). After stirring overnight at room temperature, to the mixture was added water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate=70/30 to 30/70) to give the title compound (89.7 g, 250 mmol, 99%).

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified with silica gel column (hexane/ethyl acetate=70/30 to 30/70)

출처 및 근거

ORD 기록
ord-b59673d570cf48c78b6d783fc4727013
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541585B2

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