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

HRID 1193371Notes

Reaction equation

HRID 1193371 reaction equation
O=[C: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.CN.Cl.[BH3-][C:19]#[N:20].[Na+]>CO.CC(O)=O>[CH3:19][NH:20][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

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.126 mmol, 1.0 eq.) was dissolved in MeOH (50 ml); AcOH (2 drops) and CH3NH2.HCl (2.2 g, 32.663 mmol, 1.3 eq.) were added and stirring was carried out for 2 hours at RT. NaCNBH3 (3.11 g, 50.25 mmol, 2.0 eq.) was added in portions at 0° C. and the mixture was stirred for 14 hours at RT. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography (Alox, 3% MeOH in DCM). Yield: 55% (3.0 g, 14.019 mmol)

Workup

  1. stirringthe mixture was stirred for 14 hours at RT
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography (Alox, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-f738bd263d9f4954aa213eb17c3715c1
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…