Diethyl Ether → Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}(3,5-difluorophenyl)acetate

HRID 602656Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[C:4](=[C:13]1[CH2:16][N:15]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14]1)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1.[BH4-].[Na+].CCOCC>CO.C(Cl)Cl>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[N:15]2[CH2:14][CH:13]([CH:4]([C:5]3[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([F:11])[CH:10]=3)[C:3]([O:2][CH3:1])=[O:32])[CH2:16]2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5.0 g (10.54 mmol) of methyl{1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate in 60 mL of MeOH and 15 mL of CH2Cl2 was slowly added 798 mg (21.08 mmol) of NaBH4. The solution was stirred for 5 h at 0° C., then poured into 250 mL of ether and washed with 50 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound; 1NMR (CDCl3) δ 2.68 (m, 1H), 2.92 (m, 1H), 3.10-3.15 (m, 2H), 3.44 (m, 1H), 3.69 (s, 3H), 3.86 (d, J=11 Hz, 1H), 4.30 (s, 1H), 6.74 (m, 1H), 6.85 (m, 2H), 7.24-7.34 (m, 8H); Mass Spectrum: m/e=476 (M+1 35Cl, 35Cl) and 478 (M+1 35Cl, 37Cl).

Workup

washwashed with 50 mL of aq NaHCO3
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record: ord-3866e28584b8435c90c57a85db3500cd
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906503B2

Reaction notes

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