Boron tribromide → {1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanol

HRID 1180768노트

반응식

HRID 1180768 반응식
C([O:8][CH2:9][C:10]1([CH2:14][C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:13][CH2:12][CH2:11]1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[C:20]1([C:18]2[N:19]=[C:15]([CH2:14][C:10]3([CH2:9][OH:8])[CH2:13][CH2:12][CH2:11]3)[S:16][CH:17]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 112102692-({1-[(Benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole

생성물 1

HCID 11737047{1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanol수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.7 g (2.0 mmol) of 2-({1-[(benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole in 15 mL of dichloromethane was added a 1.0 M solution of 2.2 mL (2.2 mmol) of boron tribromide and the contents stirred at room temperature for 16 h. After quenching with 10 mL of methanol, the contents were concentrated under vacuum and the residue was purified by silica gel chromatography using ethyl acetate:hexane (1:9) as the eluent to afford 0.16 g (31%) of {1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 4.13 (t, J=7 Hz, 1H), 3.66 (d, J=6 Hz, 2H), 3.3 (s, 2H), 2.08-1.94 (m, 6H). GC-MS m/z 260 (M+H).

후처리

  1. customAfter quenching with 10 mL of methanol
  2. concentrationthe contents were concentrated under vacuum
  3. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-b719fed585324370beb4d16dd26749cb
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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