Boron tribromide → (R)-3-(N,N-Dicyclobutylamino)-8-fluoro-5-hydroxy-3,4-dihydro-2H-1-benzopyran

HRID 52270ノート

反応式

HRID 52270 の反応式
Cl.[F:2][C:3]1[C:12]2[O:11][CH2:10][C@H:9]([N:13]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH2:8][C:7]=2[C:6]([O:22]C)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[F:2][C:3]1[C:12]2[O:11][CH2:10][C@H:9]([N:13]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH:18]3[CH2:19][CH2:20][CH2:21]3)[CH2:8][C:7]=2[C:6]([OH:22])=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 70147232(R)-8-Fluoro-3-(N,N-dicyclobutylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride

生成物 1

HCID 22871229(R)-3-(N,N-Dicyclobutylamino)-8-fluoro-5-hydroxy-3,4-dihydro-2H-1-benzopyran収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-40 °C

実験手順

(R)-8-Fluoro-3-(N,N-dicyclobutylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride (0.77 g, 2.26 mmol) was dissolved in anhydrous CH2Cl2 (20 mL) and cooled to -40° C. To the solution was BBr3 (0.54 mL, 5.7 mmol), dissolved in anhydrous CH2Cl2 (3 mL), added dropwise. The cooling-bath was removed and after 2 h at room temperature the reaction was completed. The reaction was poured out onto an ice/2M NH3 solution and the mixture was extracted, twice, with (MgSO4), filtered, and the solvent removed in vacuo to diethyl ether. The combined ether portions were dried give the crude residue. Chromatography on silica (eluent: 50% ethyl acetate/hexane) gave 0.58 g (89% yield) of the title compound as a white solid. Mp: 170°-2° C. [α]21D =-114.4° (C=0.1; CHCl3) GC-MS (70 eV) M=291 (2%).

後処理

  1. additionadded dropwise
  2. customThe cooling-bath was removed and after 2 h at room temperature the reaction
  3. additionThe reaction was poured out onto an ice/2M NH3 solution
  4. extractionthe mixture was extracted
  5. filtrationtwice, with (MgSO4), filtered
  6. customthe solvent removed in vacuo to diethyl ether
  7. dry with materialThe combined ether portions were dried
  8. customgive the crude residue

出典と根拠

ORDレコード
ord-340fe5526c274f7aa73eec05c2fe8b8f
出典データセット
uspto-grants-1997_04
特許番号
US05616610

反応ノート

読み込み中…