(3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide → 1-phenyl-N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine

HRID 1366558Notes

Reaction equation

O=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:6]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH2:5][O:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>COCCOC>[C:19]1([CH2:18][NH:17][CH2:15][C@@H:6]2[CH2:5][O:4][CH2:3][CH2:2][N:7]2[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide (6.3109 g, 19.45 mmol) in 1,2-dimethoxyethane (100 mL) was added LiAlH4 (2.6 g, 68.51 mmol). The mixture was heated at 100° C. and stirred for 6 h, and then cooled to 60° C. and stirred overnight. The mixture was cooled to 0° C. and quenched by slow addition of 1 N aq. NaOH (100 mL). The mixture was extracted with Et2O (2×150 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by gradient silica gel chromatography (1% to 5% MeOH in DCM) to give 1-phenyl-N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine (3.8342 g, 66%) as a light yellow oil. LCMS: (M+H)+: 297.1.

Workup

temperaturecooled to 60° C.
stirringstirred overnight
temperatureThe mixture was cooled to 0° C.
customquenched by slow addition of 1 N aq. NaOH (100 mL)
extractionThe mixture was extracted with Et2O (2×150 mL)
dry with materialthe combined organic phase was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by gradient silica gel chromatography (1% to 5% MeOH in DCM)

Sources & evidence

ORD record: ord-314c42690b634b689e8ec5b7336546e8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

Loading…