Bromomethylcyclopropane → HCID 42625935, compound

HRID 1875579Notes

Reaction equation

HRID 1875579 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 11,174.5%

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 (0.031 9 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-20e342ae00774928a4c11bbc6be6be57
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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