N-Methylbenzylamine → HCID 67424100, compound

HRID 1172217Notes

Reaction equation

[C:1]1([C@:7]23[CH2:12][C@H:11]2[CH2:10][O:9][C:8]3=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:18]([NH:25][CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.C1COCC1>[CH2:18]([N:25]([CH3:26])[C:8]([C@@:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][C@H:11]1[CH2:10][OH:9])=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1S,5R)-1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one (10.5 g, 60.0 mmol) in CH2Cl2 (200 mL) was added AlCl3 (16.0 g, 120 mmol) and then the mixture was cooled to 0° C., and then benzyl methyl amine (240 mmol, as a 2.0M solution of benzyl methyl amine in THF) was added slowly. The mixture was stirred at room temperature for 24 h, and then the reaction was quenched with saturated aqueous NH4Cl. After addition of CH2Cl2 and H2O, the resulting mixture was partitioned. The organic layer was washed with 1N HCl and brine, dried (Na2SO4), evaporated, and purified by column chromatography (silica gel; AcOEt/hexane, 1:4) to give (1S,2R)-2-Hydroxymethyl-1-phenyl-cyclopropanecarboxylic acid benzyl-methyl-amide.

Workup

customthe reaction was quenched with saturated aqueous NH4Cl
additionAfter addition of CH2Cl2 and H2O
customthe resulting mixture was partitioned
washThe organic layer was washed with 1N HCl and brine
dry with materialdried (Na2SO4)
customevaporated
custompurified by column chromatography (silica gel; AcOEt/hexane, 1:4)

Sources & evidence

ORD record: ord-be1ecf883b0c455596657a8585b6c561
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834008B2

Reaction notes

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