4'-Chloro-3'-methylacetophenone → 1-{3-[1-(4-Chloro-3-methyl-phenyl)-ethylamino]-benzyl}-azetidine-3-carboxylic acid methyl ester

HRID 1629698Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:6]1)=[O:4].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH3:25])=[CH:20][C:19]=1[CH3:27].[B][B][B][B][B][B][B][B][B][B]>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:24]([C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[C:19]([CH3:27])[CH:20]=3)[CH3:25])[CH:11]=2)[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of INT 3 (220 mg, 0.99 mmol) and 1-(4-chloro-3-methyl-phenyl)-ethanone (202 mg, 1.20 mmol) in MeOH (10 mL) was added decaborane (85 mg, 0.70 mmol). The mixture was stirred at 60° C. overnight. More decaborane (85 mg, 0.70 mmol) was added and the mixture was stirred at 60° C. for an additional 3 hours. The mixture was concentrated. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH) to afford INT 4.

Workup

stirringthe mixture was stirred at 60° C. for an additional 3 hours
concentrationThe mixture was concentrated
customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH)
customto afford INT 4

Sources & evidence

ORD record: ord-999c31faa8f64458826867500c500609
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791100B2

Reaction notes

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