Water → 3-Hexyl-6-phenyl-3-azabicyclo[3.1.0]hexane

HRID 428850Notes

Reaction equation

[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([CH:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([CH:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-hexyl-6-phenyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 27, 40 mg, 0.15 mmol) in anhydrous tetrahydrofuran (2 ml) at room temperature under nitrogen, was added dropwise a solution of lithium aluminium hydride 1.0 M in tetrahydrofluran (0.3 ml, 0.3 mmol), then the mixture was heated to 60° C. for 4 hours, cooled and stirred at room temperature for 64 hours. Water (30 ml) was carefully added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (30 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (1.5 g) column chromatography eluting with 80:20:1 ethyl acetate:hexane:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (14 mg, 38%).

Workup

temperaturecooled
extractionthe mixture was extracted with ethyl acetate (2×25 ml)
washThe combined extracts were washed with water (30 ml)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica (1.5 g) column chromatography
washeluting with 80:20:1 ethyl acetate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8ad52ac3fa1844d6a3064cdb607c673c
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313312B1

Reaction notes

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