Water → tert-Butyl 4-[(methanesulfonyl)amino]piperidine-1-carboxylate

HRID 751657Notes

Reaction equation

HRID 751657 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].N1C=CC=CC=1.O>ClCCl>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 47464928tert-Butyl 4-[(methanesulfonyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-amino-1-Boc-piperidine (300 mg, 1.50 mmol) in dichloromethane (2.0 mL) was added a solution of methanesulfonyl chloride (348 μL, 4.49 mmol) in dichloromethane (1 mL) followed by a solution of pyridine (485 μL, 5.99 mmol) in dichloromethane (1 mL), and the reaction stirred at rt for 16 h. Water (10 mL) was added, the mixture separated and the organic layer washed with 1M HCl (10 mL), sodium bicarbonate solution (10 mL) then brine (2×10 mL). The solution was dried (MgSO4) and solvent removed in vacuo. The crude material was purified by chromatography using dichloromethane/methanol (95:5) as the eluent to give the title compound as an off-white powder. δH (CD3OD): 4.46–4.40 (1H, m), 4.09–3.97 (2H, m), 3.53–3.40 (1H, m), 3.0 (3H, s), 2.93–2.81 (2H, m), 2.01–1.93 (2H, m), 1.50–1.37 (2H, m).

Workup

  1. customthe mixture separated
  2. washthe organic layer washed with 1M HCl (10 mL), sodium bicarbonate solution (10 mL)
  3. dry with materialThe solution was dried (MgSO4) and solvent
  4. customremoved in vacuo
  5. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-23884468068d42eea570c984c3310624
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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