Benzyl Bromide → (1R,7S)-3-benzyl-1,10,10-trimethyl-4-phenyl-3,4-diazatricyclo[5.2.1.02,6]dec-2(6)-en-5-one

HRID 1437911Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([N:15]2[C:23](=[O:24])[C:22]3[C@@H:21]4[C:25]([CH3:27])([CH3:26])[C@@:18]([CH3:28])([CH2:19][CH2:20]4)[C:17]=3[NH:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C=O.[OH-].[Na+]>[CH2:1]([N:16]1[C:17]2[C@@:18]3([CH3:28])[C:25]([CH3:27])([CH3:26])[C@H:21]([CH2:20][CH2:19]3)[C:22]=2[C:23](=[O:24])[N:15]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of benzyl bromide (0.54 mL, 4.5 mmol) and (4S,7R)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 1.11 g, 4.1 mmol) in N,N-dimethylformamide was heated at 78° C. for 2.5 h. The reaction mixture was diluted with 1 M NaOH (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 M NaOH and brine, dried (magnesium sulfate), filtered and evaporated. The residue was recrystallized from ethyl acetate/hexanes to give (4S,7R)-1-benzyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (114 mg, 8%) as a tan solid. APCI-MS (M+H) 359.

Workup

extractionextracted with ethyl acetate (200 mL)
washThe organic layer was washed with 1 M NaOH and brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
customevaporated
customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-83ae9d14c5e94622ab9e9178c356c9c9
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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