Water → 1-Azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol

HRID 499657Notes

Reaction equation

[N:1]12[CH2:7][C:4]([C:8]([O:10]CC)=O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1COCC1>[N:1]12[CH2:7][C:4]([C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:10])([CH2:3][CH2:2]1)[CH2:5][CH2:6]2

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate (4 g, 23 mmol) in THF (60 mL) was added dropwise to a solution of phenyllithium (1.5 M in 70% cyclohexane/30% diethyl ether, 63.1 mL, 94.6 mmol) pre-cooled to −30° C. under Ar. The reaction was warmed to RT and stirred for 16 h. The reaction was treated with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Trituration (diethyl ether) afforded the title compound (3.595 g, 54%). EI-MS m/z 280 (MH)+ Rt (1.56 min).

Workup

temperatureThe reaction was warmed to RT
extractionextracted with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b66fbf5259e346c88297ba2e4ee9aacf
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767691B2

Reaction notes

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