Bromomethylcyclopropane → HCID 42625935, compound

HRID 2283030Notes

Reaction equation

HRID 2283030 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

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

Product 1

HCID 42625935HCID 42625935, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 (0.0319 g, 39.9%). EI-MS m/z 348 (M+) Rt (1.69 min).

Workup

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

Sources & evidence

ORD record
ord-e4b409560d6b4f81a5a46bd0fc8ed6a4
Source dataset
uspto-grants-2015_09
Patent number
US09144571B2

Reaction notes

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