m-Chloroperbenzoic acid → (3R)-3-(Benzylsulfinyl)methyl-1-(tert-butoxycarbonyl)pyrrolidine

HRID 1459721Notes

Reaction equation

[CH2:1]([S:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:27].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:1]([S:8]([CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (3R)-3-(benzylthio)methyl-1-(tert-butoxycarbonyl)pyrrolidine (0.2553 g, 0.830 mmol) in ethyl acetate (15 ml), under argon, cooled in a bath at ca. -40° C., was added portionwise 57-86% 3-chloroperoxybenzoic acid (0.2094 g). The mixture was then allowed to warm to 0° C. over 1.5 h, before pouring into 5% NaHCO3 solution (15 ml). The organic layer was separated and washed with more 5% NaHCO3 solution (15 ml), then saturated NaCl solution (10 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2) to give 0.2381 g (89%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.44 (9H, s), 1.61 (1H, m), 2.15 (1H, m), 2.52 (1H, m), 2.66 (2H, m), 3.00 (1H, m), 3.29 (1H, m), 3.43 (1H, m), 3.63 (1H, m), 3.96 (1H, d, J=12.9 Hz), 4.07 (1H, d, J=12.9 Hz), 7.28-7.30 (2H, m), 7.35-7.39 (3H, m). m/e (ES+) 324 (M+H)+.

Workup

customThe organic layer was separated
washwashed with more 5% NaHCO3 solution (15 ml)
dry with materialsaturated NaCl solution (10 ml), dried (MgSO4)
customevaporated in vacuo
customThe residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-a738c16b3a164b7386326527bbd9d776
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854268

Reaction notes

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