Triethylamine → Tert-butyl (1-(methylsulfonyl)piperidin-3-yl)methylcarbamate

HRID 2168016Notes

Reaction equation

HRID 2168016 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C>ClCCl>[CH3:16][S:17]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:2]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2756030tert-butyl N-[(piperidin-3-yl)methyl]carbamate

Product 1

HCID 47411127Tert-butyl (1-(methylsulfonyl)piperidin-3-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl piperidin-3-ylmethylcarbamate (500 mg) was dissolved in anhydrous dichloromethane (10 mL), and methanesulfonyl chloride (0.181 mL) was added followed by the addition of triethylamine (1.3 mL). The reaction mixture was stirred at room temperature overnight. The organic solvent was removed under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 0-70% ethyl acetate in hexane to give the title compound.

Workup

  1. customThe organic solvent was removed under vacuum
  2. customThe residue was purified with flash column chromatography on silica gel eluting with 0-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-56d92eb8868548be83e7c69ffd25d95a
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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