Pyridine → Ethyl N-tert-butoxycarbonyl-4-[3-(methane-sulfonylaminomethyl)benzyl]piperidine-4-carboxylate

HRID 1068447Notes

Reaction equation

HRID 1068447 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:19](C)[C:20]2[CH:25]=[CH:24][CH:23]=[C:22](N)[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][S:29](Cl)(=[O:31])=[O:30].[N:33]1C=CC=C[CH:34]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:34][NH:33][S:29]([CH3:28])(=[O:31])=[O:30])[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 70205512ethyl N-tert-butoxycarbonyl-4-(3-amino-methylbenzyl)piperidine-4-carboxylate

Product 1

HCID 70204744Ethyl N-tert-butoxycarbonyl-4-[3-(methane-sulfonylaminomethyl)benzyl]piperidine-4-carboxylate

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl N-tert-butoxycarbonyl-4-(3-amino-methylbenzyl)piperidine-4-carboxylate (400 mg, 0.106 mmol) and methanesulfonyl chloride (99 μL, 0.127 mmol) in anhydrous pyridine (4 mL) was heated at 70° C. for 4 h. The resultant mixture was concentrated, and the residue was subjected to column chromatography on silica gel eluting with 50% ethyl acetate in hexane. Collection and concentration of appropriate fraction provided the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated
  2. customCollection and concentration of appropriate fraction

Sources & evidence

ORD record
ord-3202d73586e7485b81fad2c6d3a6d8d2
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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