Ammonium Chloride → HCID 10686038, compound

HRID 1975649Notes

Reaction equation

[CH:1](=[C:8]1[C:13](=[O:14])[CH:12]2[CH2:15][CH2:16][N:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Mg]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C(OCC)C>[C:2]1([CH:1]([CH:8]2[C:13](=[O:14])[CH:12]3[CH2:11][CH2:10][N:9]2[CH2:16][CH2:15]3)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a stirred solution of 2-benzylidene-3-oxo-1-azabicyclo[2.2.2]octane (10 g) in diethyl ether (200 ml) at -10° C. under a nitrogen atmosphere was added a solution of 2M-benzylmagnesium chloride (30 ml, in tetrahydrofuran, 50 mmol) and diethyl ether (100 ml). The solution was stirred at -10° C. for 30 minutes and at ambient temperature for 16 h. A saturated solution of aqueous ammonium chloride (200 ml) was carefully added and the product extracted into ethyl acetate. The organic phase was dried (MgSO4) and evaporated to dryness. The residue was chromatographed on a column containing silica gel 60 (220-440 mesh ASTM) eluting with mixtures of 30%, 50% and 70% ethyl acetate in petroleum ether (bp 60°-80° C.). 2-(1,2-diphenylethyl)-3-oxo1- azabicyclo [2.2.2]octane was obtained as 1:1 mixture of stereoisomers by evaporating the appropriate fractions.

Workup

extractionthe product extracted into ethyl acetate
dry with materialThe organic phase was dried (MgSO4)
customevaporated to dryness
customThe residue was chromatographed on a column
additioncontaining silica gel 60 (220-440 mesh ASTM)
washeluting with mixtures of 30%, 50% and 70% ethyl acetate in petroleum ether (bp 60°-80° C.)

Sources & evidence

ORD record: ord-830ad8c947a84d5bb55f6c5af3b82ade
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288730

Reaction notes

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