Water → tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

HRID 30102Notes

Reaction equation

HRID 30102 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>O1CCCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 25250149tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of piperidin-4-yl-carbamic acid tert-butyl ester (1.0 g, 5.0 mmol, Astratech, Inc.) and diisopropylethylamine (4 mL) in tetrahydrofuran (40 mL) was stirred at +5° C. To this was added methanesulfonyl chloride (1.0 g, 8.8 mmol) in a bolus. The reaction was brought to room temperature for 1 hour, poured into water and extracted into methylene chloride (2×50 mL). The combined organic extracts were washed with 5% aqueous sodium bicarbonate. The organic solution was dried (Na2SO4) and solvent was removed under vacuum to give a crude solid. Purification was by trituration with ether/hexane to give (1-methanesulfonyl-piperidin4-yl)-carbamic acid tert-butyl ester as a white solid. Mass spectrum (ES) H+: 278

Workup

  1. extractionextracted into methylene chloride (2×50 mL)
  2. washThe combined organic extracts were washed with 5% aqueous sodium bicarbonate
  3. dry with materialThe organic solution was dried (Na2SO4) and solvent
  4. customwas removed under vacuum
  5. customto give a crude solid
  6. customPurification

Sources & evidence

ORD record
ord-e58e6e37e13c4fbd8bf4492a8b73316c
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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