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

HRID 52270노트

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HRID 52270 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-40 °C

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-340fe5526c274f7aa73eec05c2fe8b8f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616610

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