3-Amino-1-propanol → HCID 61637468, compound

HRID 1619795Notes

Reaction equation

HRID 1619795 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][CH2:16][CH2:17][CH2:18][OH:19]>CO.[Pd]>[OH:19][CH2:18][CH2:17][CH2:16][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

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 61637468HCID 61637468, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 3-oxo-1-piperidinecarboxylate (5.0 g, 25.1 mmol) and 3-amino-1-propanol (5.66 mL, 73.8 mmol) in MeOH (75 mL) was hydrogenated over 10% Pd on C (200 mg) for 1 day (Yokoyama et al., Bioorg. Med. Chem. 2008, 16, 7968) to give tert-butyl 3-[(3-hydroxypropyl)amino]-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) (rotamers) δ 3.80 (t, J=5.1 Hz, 2H), 3.80 (br, 1H), 3.65 and 3.67 (2t, J=4.7 Hz, 1H), 3.06-2.86 (m, 4H), 2.62-2.56 (m, 1H), 1.90-1.86 (m, 1H), 1.72-1.62 (m, 3H), 1.50-1.30 (m, 2H), 1.46 (s, 9H).

Sources & evidence

ORD record
ord-68f84e6444a8442ba9caefc031717f23
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

Loading…