Triethylamine → (S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester

HRID 906464Notes

Reaction equation

HRID 906464 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 10469651(S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.48 mL) was added to a solution of (S)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (1.10 g) and triethylamine (1.42 mL) in DCM (20 mL) at 0° C. under nitrogen. The reaction was stirred for 2 h before being partitioned between DCM (200 mL) and water (100 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the subtitle product (1.20 g) as a yellow oil.

Workup

  1. custombefore being partitioned between DCM (200 mL) and water (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-81c6bd324ffa4e9b8490682ebddcfe38
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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