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

HRID 1276487

Reaction equation

HRID 1276487 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-283c4b46e9ad413f8231c0039d86a99f
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Linked notes

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