Water → 2-(4-Benzylmorpholin-2-yl)ethan-1-ol

HRID 1608216Notes

Reaction equation

C([O:3][C:4]([CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>C(OCC)C>[OH:3][CH2:4][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-ethoxycarbonylmethyl-4-benzylmorpholine (41 g) in diethyl ether (100 ml) is added dropwise to a stirred suspension of lithium aluminum hydride (59.2 g) in diethyl ether (150 ml). The reaction mixture is stirred at 25° C. for 1 hour. The excess of lithium aluminum hydride is decomposed by the successive addition of ethyl acetate and water. The insoluble materials are filtered off, and the filtrate is evaporated to give the title compound (34.4 g) as an oil. The starting material, 2-ethoxycarbonylmethyl-4-benzylmorpholine, is prepared according to the method of F. Loftus [Syn. Commun., 10, 59-73 (1980)].

Workup

filtrationThe insoluble materials are filtered off
customthe filtrate is evaporated

Sources & evidence

ORD record: ord-38c5b70e8f36445eab66d2f41d246acf
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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