Pyridine → 1-(Tert-butoxycarbonyl)-4-methyl-4-(methanesulfonyloxymethyl)piperidine

HRID 1986178Notes

Reaction equation

HRID 1986178 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][OH:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][O:16][S:24]([CH3:23])(=[O:26])=[O:25])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidine

Product 1

HCID 222480521-(Tert-butoxycarbonyl)-4-methyl-4-(methanesulfonyloxymethyl)piperidineYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-hydroxymethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (1.25 g, 5.45 mmol) and pyridine (0.661 mL, 8.18 mmol) in dichloromethane (10 mL) at 0° C. is added methanesulfonyl chloride (0.593 mL, 7.63 mmol). After 3 hours, one additional equivalent of methanesulfonylchloride and pyridine are added. After 1 hour the reaction mixture is concentrated, then EtOAc and water are added. The organic layer is concentrated and chromatographed on silica gel eluting with MeOH in dichloromethane 0-3% to give the title compound as a yellow oil (1.60 g, 95% yield).

Workup

  1. concentrationAfter 1 hour the reaction mixture is concentrated
  2. additionEtOAc and water are added
  3. concentrationThe organic layer is concentrated
  4. customchromatographed on silica gel eluting with MeOH in dichloromethane 0-3%

Sources & evidence

ORD record
ord-d3956a8161a44461a8a71f7bedd6e85e
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

Loading…