Bromomethylcyclopropane → HCID 42625935, compound

HRID 1724891Notes

Reaction equation

[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:23][CH2:24][CH:25]1[CH2:27][CH2:26]1>CC#N>[Br-:23].[CH:25]1([CH2:24][N+:1]23[CH2:6][CH2:5][C:4]([C:9]([OH:10])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)([CH2:3][CH2:2]2)[CH2:7][CH2:8]3)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0552 g, 0.188 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) was added (bromomethyl)cyclopropane (0.025 mL, 0.257 mmol). The solution was heated at 60° C. for 16 h, cooled down to room temperature and the solvents evaporated under vacuum. The residue was taken up in 2.5 mL of DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.031 9 g, 39.9%). EI-MS m/z 348(M+) Rt (1.69 min).

Workup

temperaturecooled down to room temperature
customthe solvents evaporated under vacuum
custompurified by preparatory HPLC (without TFA)

Sources & evidence

ORD record: ord-a7bae74be90d4ae9a472b3d9b1d46f32
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488827B2

Reaction notes

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