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

HRID 574832Notes

Reaction equation

HRID 574832 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-6afd9f6c1aa74cc39086dcc516739c0e
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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