Lithium borohydride → HCID 86301335、化合物

HRID 513939ノート

反応式

HRID 513939 の反応式
[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

参加物

5

反応物 3

HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydride2 回HCID 86301334HCID 86301334、化合物

生成物 1

HCID 86301335HCID 86301335、化合物収率 38%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b03291b728fe441396755bc09ee00cbc
出典データセット
uspto-grants-2015_08
特許番号
US09102674B2

反応ノート

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