Triethylamine → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 222574

Reaction equation

HRID 222574 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.C(N(CC)CC)C>ClCCl>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Methanesulfonyl chloride (29.26 g, 19.77 mL, 255.47 mmol) is added slowly (10 min) under nitrogen atmosphere to a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (50.00 g, 232.24 mmol) and triethylamine (35.25 g, 48.56 mL, 348.36 mmol) in anhydrous dichloromethane (700 mL) at 9° C. (internal temperature). The mixture is stirred at 23° C. for 16 h. The reaction mixture is successively washed with 1 M aq hydrochloric acid, water, and brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and the solvent is removed to obtain 60 g of the title compound as a white solid. MS (m/z) 316 (M+23).

Workup

  1. washThe reaction mixture is successively washed with 1 M aq hydrochloric acid, water, and brine
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-1f2372b8945d49749af2ffa4d7f146cf
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Linked notes

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