Methanol → HCID 68972697, compound

HRID 1726182Notes

Reaction equation

HRID 1726182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=2)[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:32][O:33][S:34]([O-:36])=O.[K+].[CH3:38]O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=2)[C:15]2[CH:16]=[CH:17][C:18]([S:34]([CH3:38])(=[O:36])=[O:33])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4].[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=2)[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:22])=[O:32])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 68968817HCID 68968817, compound

Product 2

HCID 68971705HCID 68971705, compoundYield 32%HCID 68972697HCID 68972697, compoundYield 53%

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[(3-cyano-benzyl)-(4-methylsulfanyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 105) (484 mg, 1.1 mmol) in MeOH (20 mL) cooled to 0° C. was added OXONE® (680 mg, 1.1 mmol) and the mixture was stirred at 0° C. for 1.5 hours. Work-up and purification afforded 4-[(3-cyano-benzyl)-(4-methanesulfonyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (166 mg, 32%) as a white solid and 4-[(3-cyano-benzyl)-(4-methanesulfinyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (264 mg, 53%) as a white solid.

Workup

  1. customWork-up and purification

Sources & evidence

ORD record
ord-80027c504f404887b3cc7d6a8033bf89
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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