4-Toluenesulfonyl chloride → (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

HRID 272713

반응식

HRID 272713 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>CN(C)C1C=CN=CC=1.ClCCl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:11][CH2:10][C@H:9]2[CH2:12][CH2:13][CH2:14][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])(=[O:23])=[O:22])=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

생성물 1

HCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate수율 45%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

A mixture of Boc-D-prolinol (201 mg, 1.0 mmol), p-toluenesulfonyl chloride (400 mg, 2.1 mmol), triethylamine (420 μL, 3.0 mmol), and 4-(dimethylamino)pyridine (12 mg, 0.1 mmol) in dichloromethane (10 mL) was heated at 40° C. for 48 hours, cooled to room temperature, concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated. The residue was purified by column chromatography on silica gel to provide 160 mg (45%) of the desired product.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-d63fff0499e247fd9dceeb7f7da20f56
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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