4-Toluenesulfonyl chloride → 1-Tosyl-3-pyrrolidinol Tosylate

HRID 2371877노트

반응식

HRID 2371877 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1>N1C=CC=CC=1>[S:7]([N:15]1[CH2:16][CH2:17][CH:13]([O:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:14]1)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 982104-Hydroxypyrrolidine

생성물 1

HCID 150203551-Tosyl-3-pyrrolidinol Tosylate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Para-toluenesulphonyl chloride (68.8 g) was added, in portions, to a solution of 3-(R,S)-hydroxypyrrolidine (15 g) in dry pyridine (200 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solution was concentrated in vacuo to approximately half the original volume then partitioned between dichloromethane (500 ml) and water (300 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (3×100 ml). The combined dichloromethane extracts were washed with 2M hydrochloric acid (100 ml) and 10% aqueous sodium hydroxide (100 ml) then dried (MgSO4) and concentrated in vacuo to give an oil which was crystallised from dichloromethane/ether to give the title compound as a microcrystalline powder, yield 28.3 g, m.p. 119°-121° C.

후처리

  1. concentrationThe solution was concentrated in vacuo to approximately half the original volume
  2. customthen partitioned between dichloromethane (500 ml) and water (300 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×100 ml)
  5. washThe combined dichloromethane extracts were washed with 2M hydrochloric acid (100 ml) and 10% aqueous sodium hydroxide (100 ml)
  6. dry with materialthen dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas crystallised from dichloromethane/ether

출처 및 근거

ORD 기록
ord-40574ea15a8c429c9008129cc556a547
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05096890

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