Diisobutylaluminum hydride → Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate
Reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH2:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([CH2:3][OH:2])[CH2:6][CH2:7]1)=[O:12])[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
The above ester (12.8 g, 59.5 mmol, 1.0 equiv) was dissolved in 50 mL of dry CH2Cl2 under Ar and cooled to −78° C. A 1 Molar solution of DIBAL-H in CH2Cl2 (149 mL, 149 mmol, 2.5 equiv) was added dropwise over a 30 min period. The cold bath was removed and the reaction solution allowed to warm to ambient temperature. At this time EtOAc (10 mL) was added dropwise to quench the excess DIBAL-H. 100 mL of 1H HCl (aq) was added dropwise over a 30 min period with rapid stirring. The resulting mixture was filtered on a pad of diatomaceous earth and the filtrate was dried over Na2SO4, decanted and concentrated to yield 4-hydroxymethyl-piperidine-1-carboxylic acid ethyl ester as a nearly colorless oil that was used without further purification.