Triethylsilane → 4-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1'-cyclopropane]

HRID 1258836Notes

Reaction equation

[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17]([CH:20]([C:22]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=3[Cl:29])O)[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.OS(C(F)(F)F)(=O)=O>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17]([CH2:20][C:22]3[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=3[Cl:29])[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To an ice cold solution of (4-benzylspiro[3H-1,4-benzoxazine-2,1-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol (780 mg, 1.7 mmol) in trifluoroacetic acid (4 mL) was added triethylsilane (1.32 mL, 8.3 mmol) followed by triflic acid (0.15 mL, 1.7 mmol). After heating the mixture for 15 min at 50° C., the reaction was cooled to room temperature. Trifluoroacetic acid was evaporated under reduced pressure, and the resulting residue was taken in saturated aq. sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography to furnish 4-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1-cyclopropane] (715 mg).

Workup

temperaturethe reaction was cooled to room temperature
customTrifluoroacetic acid was evaporated under reduced pressure
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9a5d4fa348524a2ba827c92400fa11d3
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466114B2

Reaction notes

Loading…