Lithium borohydride → HCID 86301335, 화합물

HRID 513939노트

반응식

HRID 513939 반응식
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([CH:18]([OH:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydride2회HCID 86301334HCID 86301334, 화합물

생성물 1

HCID 86301335HCID 86301335, 화합물수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled solution, 0° C., of 1-(7-((4-fluorobenzyl)oxy)quinolin-3-yl)ethanone (Example 42, 53 mg, 0.18 mmol) in THF was added NaBH4 (8 mg, 0.24 mmol). The reaction mixture was stirred for 1 hour. A further portion of NaBH4 (20 mg, 0.59 mmol) was added and stirred for 30 minutes at 0° C. LiBH4 (50 mg, 2.30 mmol) was added and the reaction was stirred for 15 minutes before being quenched with sat. NH4Cl (aq.) solution. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and concentrated under reduced pressure onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a white solid (20 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=1.6 Hz, 1H), 8.10 (s, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.53-7.43 (m, 3H), 7.31-7.26 (m, 1H), 7.09 (t, J=8.6 Hz, 2H), 5.17 (s, 2H), 5.12 (q, J=6.5 Hz, 1H), 1.62 (d, J=6.7 Hz, 3H). [M+H]=298.3.

후처리

  1. stirringstirred for 30 minutes at 0° C
  2. stirringthe reaction was stirred for 15 minutes
  3. custombefore being quenched with sat. NH4Cl (aq.) solution
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated under reduced pressure onto silica
  7. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

출처 및 근거

ORD 기록
ord-b03291b728fe441396755bc09ee00cbc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102674B2

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