Water → tert-Butyl 3-[(propan-2-yl)amino]piperidine-1-carboxylate

HRID 919587Notes

Reaction equation

HRID 919587 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[NH2:15][CH:16]([CH3:18])[CH3:17].[BH4-].[Na+].O>CO.C(Cl)Cl>[CH:16]([NH:15][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 53346644tert-Butyl 3-[(propan-2-yl)amino]piperidine-1-carboxylateYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-oxopiperidine-1-carboxylate (2 g, 10.03 mmol) and 2-aminopropane (710 mg, 12.04 mmol) in MeOH (40 mL) was stirred at rt for 1 h. To the solution was added NaBH4 (758 mg, 20.06 mmol) at 0° C. and the reaction mixture was stirred at rt for 12 h. The reaction mixture was diluted with ice-cooled water and the solvent was reduced to afford a residue which was dissolved in CH2Cl2 and washed with water. The organic layer was dried over Na2SO4, concentrated in vacuo and purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (2 g, 82%). 1H NMR (400 MHz, CDCl3): δ 4.01-3.90 (m, 1H), 3.78 (dt, J=3.6, 9.2 Hz, 1H), 3.48 (s, 1H), 2.96 (heptate, 0.1=6.4 Hz, 1H), 2.92-2.79 (m, 1H), 2.69-2.55 (m, 1H), 1.90-1.87 (m, 1H), 1.68-1.61 (m, 1H), 1.46 (s, 9H), 1.29-1.18 (m, 2H), 1.05 (d, J=6.0 Hz, 6H). ES-MS: m/z [M+1]=243.

Workup

  1. additionThe reaction mixture was diluted with ice-
  2. customto afford a residue which
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d16ade6e5a7841859d753139f35fab8f
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…