Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine

HRID 1276487

반응식

HRID 1276487 반응식
[OH:1][CH2:2][CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][NH:5][CH2:4]1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:14]1([S:20]([N:5]2[CH2:6][CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:3]([CH2:2][O:1][S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH2:4]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 13316928(4-Phenylpyrrolidin-3-yl)methanol

생성물 1

HCID 867561541-(Benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine수율 67.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A solution of 196 mg (1.1 mmol) of 3-(SR)-hydroxymethyl-4-(SR)-phenylpyrrolidine (from Example 1, Step C) and 27 mg (0.2 mmol) of 4-(N,N-dimethylamino)pyridine in 5 mL of pyridine at 0 ° C. was treated with 488 mg (2.8 mmol) of benzenesulfonyl chloride. The cooling bath was removed and the resulting mixture was stirred at rt for 1 h. The reaction mixture was treated with an additional 290 mg of benzenesulfonyl chloride and the resulting mixture was stirred at rt for 1 h. The reaction mixture was partitioned between 50 mL of ether and 20 mL of sat'd CuSO4 and the layers were separated. The organic layer was washed with 30 mL of H2O, 30 mL of sat'd NaCl, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 30 g of silica gel using3:2 v/v hexanes/ether afforded 340 mg (67%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ2.65-2.72 (m, 1H), 3.21 (dd, J=7.8, 10.3, 1H), 3.44-3.67 (6H), 6.94-7.90 (15H). Mass Spectrum (NH3-CI): m/z 458 (M+1).

후처리

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was treated with an additional 290 mg of benzenesulfonyl chloride
  3. stirringthe resulting mixture was stirred at rt for 1 h
  4. customThe reaction mixture was partitioned between 50 mL of ether and 20 mL of sat'd CuSO4
  5. customthe layers were separated
  6. washThe organic layer was washed with 30 mL of H2O, 30 mL of sat'd NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-283c4b46e9ad413f8231c0039d86a99f
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166037

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