Hydrochloric Acid → (S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 69513

반응식

HRID 69513 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 57957824(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a mixture of p-toluenesulfonyl chloride (10.0 g) in dry methylene chloride (40 mL) was added at 0° C. a solution of (S)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2.8 g) in dry methylene chloride (15 mL). DMAP (1.1 g) and triethylamine (6.1 g) was added. The mixture was stirred at 0° C. for 3 h. The reaction mixture was then allowed to reach room temperature and stirred for 12 h. The mixture was acidified with 1 N HCl. The organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine. The organic layers were dried over sodium sulfate and concentrated. The product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way; MS (ESI): 342 (M+H+).

후처리

  1. customto reach room temperature
  2. stirringstirred for 12 h
  3. washThe organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way

출처 및 근거

ORD 기록
ord-d8cf54f57ee94f80a5892740a783cffd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

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