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

HRID 2040191Notes

Reaction equation

HRID 2040191 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-054d1396c48d4de18737b43eddad6ea6
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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