Water → tert-Butyl 4-(methylamino)piperidine-1-carboxylate

HRID 1970019Notes

Reaction equation

HRID 1970019 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][NH2:16].[BH4-].[Na+].O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:15][NH:16][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateYield 55%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

3.8 mL (13 mmol) of titanium isopropoxide and 2 g (10 mmol) of 1-tert-butoxycarbonyl-piperidin-4-one are added to 3.7 mL (30 mmol) of a 33% solution of methylamine in ethanol. The solution is stirred for 5 hours at room temperature then 378 mg (10 mmol) of sodium borohydride is added. Stirring is continued for a further 2 hours then 2 mL of water is added. The reaction mixture is filtered then the solvents are evaporated to give 1.18 g (55%) of 4-methylamino-1-tert-butoxycarbonyl-piperidine in the form of an oil.

Workup

  1. stirringStirring
  2. waitis continued for a further 2 hours
  3. filtrationThe reaction mixture is filtered
  4. customthe solvents are evaporated

Sources & evidence

ORD record
ord-27a92d52647b4d4bb7ddfff2b18099dd
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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