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

HRID 392494Notes

Reaction equation

HRID 392494 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

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

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The title compound from Step A above (8.8 g, 40.87 mmoles) and triethylamine (8.55 mL, 61.31 mmoles) were dissolved in CH2Cl2 (100 mL) and the mixture was stirred under nitrogen at 0° C. Methanesulfonylchloride (3.8 mL mL, 49.05 mmoles) was added and the solution was stirred at room temperature for 2 h. The solution was diluted with CH2Cl2 and washed with saturated aqueous sodium bicarbonate, water and dried (MgSO4), filtered and evaporated to dryness to give the title compound (12.8 g) FABMS (M+1)=294.3.

Workup

  1. stirringthe solution was stirred at room temperature for 2 h
  2. washwashed with saturated aqueous sodium bicarbonate, water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7f078268d62e4e8490d587af3b058b97
Source dataset
uspto-grants-2004_10
Patent number
US06800636B2

Reaction notes

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