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

HRID 1258836노트

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HRID 1258836 반응식
[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

참가 물질

5

반응물 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 58340780(4-benzylspiro[3H-1,4-benzoxazine-2,1-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol

생성물 1

HCID 583408334-benzyl-6-[(5-bromo-2-chloro-phenyl)methyl]spiro[3H-1,4-benzoxazine-2,1'-cyclopropane]수율 92.5%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9a5d4fa348524a2ba827c92400fa11d3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466114B2

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