Aluminium lithium hydride → N-Methyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

HRID 371154Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([N:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][C@@H:13]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:33])([CH3:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][C:20]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=O)C>C(OCC)C>[CH3:10][N:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][C@@H:13]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:33])([CH3:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][C:20]=1[O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 25° C. slurry of 267 mg (7.04 mmole) of lithium aluminum hydride in 12 ml ethyl ether is added dropwise over 30 minutes a solution of 1.50 g (3.11 mmole) of N-ethoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol. The reaction is stirred for 0.5 hour at 25° C., then two hours at reflux. The reaction is quenched by addition of wet magnesium sulfate followed by decantation and washing of the salts with two 30 ml portions of ether. The ether extract is washed with 10 ml saturated sodium chloride, dried over magnesium sulfate and evaporated to give 1.19 g (91%) of the title compound as a solid.

Workup

temperaturetwo hours at reflux
customThe reaction is quenched by addition of wet magnesium sulfate
washwashing of the salts with two 30 ml portions of ether
extractionThe ether extract
washis washed with 10 ml saturated sodium chloride
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-c38c1a68572b45918b2c1cf53aa53150
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04529732

Reaction notes

Loading…