m-Chloroperbenzoic acid → HCID 53770744, compound

HRID 1459729Notes

Reaction equation

HRID 1459729 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:28]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([S:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:28])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53785514HCID 53785514, compound

Product 1

HCID 53770744HCID 53770744, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a similar method to that described in Example 107, step 1, 1-(tert-butoxycarbonyl)-4-(4-fluorobenzylthio)piperidine (1.5065 g, 4.63 mmol) was reacted with 57-86% 3-chloroperoxybenzoic acid (1.0190 g) in dichloromethane (100ml) to give 1.5287 g (97%) of the title compound as a white solid. δH (250 MHz, CDCl3) 1.46 (9H, s), 1.64-1.82 (3H, m), 2.02 (1H, m), 2.63 (1H, m), 2.81 (2H, m), 3.88 (1H, d, J=13.2 Hz), 3.98 (1H, d, J=13.2 Hz), 4.21 (2H, m), 7.08 (2H, t, J=8.6 Hz), 7.29 (2H, m); m/e (ES+) 683 (2M+H)+, 342 (M+H)+.

Sources & evidence

ORD record
ord-1cfbaeadd0d24279835b18f7f8fe9938
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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