Triethylamine → 4-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

HRID 222577Notes

Reaction equation

HRID 222577 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 232828864-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl esterYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (18.24 g, 79.54 mmol) in dichloromethane (400 mL) and triethylamine (12.20 mL, 87.49 mmol) at 0° C. is added methanesulfonyl chloride (9.23 mL, 119.30 mmol). The reaction is allowed to warm to room temperature over 16 h. The mixture is washed with 0.1 M hydrochloric acid, saturated aqueous sodium bicarbonate, water, and brine. The material is dried over magnesium sulfate, filtered, and concentrated to dryness. The crude material is purified by flash chromatography over silica gel to afford 22.65 g of the title compound as a colourless oil. 1H NMR (CDCl3) δ (ppm): 1.19-1.30 (m, 2H), 1.39 (d, 3H), 1.44 (s, 9H), 1.6-1.8 (m, 3H), 2.66 (m, 2H), 2.99 (s, 3H), 4.16 (m, 2H), 4.62 (t, 1H).

Workup

  1. washThe mixture is washed with 0.1 M hydrochloric acid, saturated aqueous sodium bicarbonate, water, and brine
  2. dry with materialThe material is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material is purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-c4f8a6aece3240a7ac0a634af8637e3e
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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