Ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate → 8-Benzyl-6-hydroxy-2,8-diazaspiro[4.5]decan-1-one
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([C:18]([O:20]CC)=O)[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH:5]1[OH:17]>CO.N>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2([C:18](=[O:20])[NH:1][CH2:2][CH2:3]2)[CH:5]([OH:17])[CH2:6]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
Into a 10000-mL 3-necked round-bottom flask was placed a solution of ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate (220 g, 718.02 mmol, 1.00 equiv) in methanol (2000 mL) and ammonia (2000 mL). The resulting solution was stirred overnight at 45° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol to obtain the title compound.