Aluminium lithium hydride → HCID 68124876, compound

HRID 1283980Notes

Reaction equation

HRID 1283980 reaction equation
C(O[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](OCC)=[O:18])[C@@H:12]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=O)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:9][N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][OH:18])[C@@H:12]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131710438HCID 131710438, compound

Product 1

HCID 68124876HCID 68124876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reduction of 8.2 g. of cis ethyl 1-benzyloxycarbonyl-2-(p-methoxybenzyl)-3-piperidinecarboxylate with 1.52 g. of lithium aluminum hydride in 97 ml. of tetrahydrofuran yielded cis-1-methyl-2-(p-methoxybenzyl)-3-piperidinemethanol, isolated as its hydrochloride (in a yield of 2.8 g.), a white crystalline solid which melted at 185°-186°C. trans-1-Methyl-2-(p-methoxybenzyl)-3-piperidinemethanol, a white crystalline solid which melted at 66°-68°C., can be obtained in similar fashion.

Sources & evidence

ORD record
ord-57c4c9bae21d430dae51e423865bbe44
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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