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

HRID 1180768ノート

反応式

HRID 1180768 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b719fed585324370beb4d16dd26749cb
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

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