m-Chloroperbenzoic acid → (3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylsulfinyl)methyl]pyrrolidine

HRID 1459725Notes

Reaction equation

HRID 1459725 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:28]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][S:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54249072(3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidine

Product 1

HCID 54513640(3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylsulfinyl)methyl]pyrrolidineYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using a similar procedure to that described in Example 107, step 1, (3R)-1-(tert-butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidine (0.5818 g, 1.79 mmol) was reacted with 57-86% 3-chloroperoxybenzoic acid (0.4477 g) in ethyl acetate (35ml) to give 0.5233 g (86%) of the title compound as a colourless oil. δH (360 MHz, CDCl3) 1.45 (9H, s), 1.66 (1H, m), 2.15 (1H, m), 2.54(1H, m), 2.63-2.71 (2H, m), 3.03 (1H, m), 3.31 (1H, m), 3.44 (1H, m), 3.65 (1H, m), 3.96 (2H, s), 7.08 (2H, t, J=8.6 Hz), 7.25-7.29 (2H, m). m/e (ES+) 342 (M+H)+.

Sources & evidence

ORD record
ord-ab5a03297b8b47828493492bbbabc3b9
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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