Sodium borohydride → HCID 90046925、化合物

HRID 1504997ノート

反応式

HRID 1504997 の反応式
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20](=[O:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(Cl)Cl>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([OH:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:6])=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 90046976HCID 90046976、化合物

生成物 1

HCID 90046925HCID 90046925、化合物収率 98.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-one (100 mg, 0.281 mmol) in MeOH (2810 μl) was added NaBH4 (13.29 mg, 0.351 mmol) at rt. This was stirred at rt for 20 min. Removed solvent in vacuo. Redissolved in DCM and quenched with sat aq NH4Cl. Separated and extracted twice more with DCM. Washed combined organics with brine, then dried on MgSO4, filtered and concentrated providing 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-ol (98.8 mg, 0.276 mmol, 98% yield) as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (d, J=6.06 Hz, 3H) 1.33 (s, 9H) 4.00-4.20 (m, 3H) 4.81 (d, J=4.29 Hz, 1H) 7.74 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.65 (s, 1H) 8.94 (d, J=4.80 Hz, 1H). MS: m/z: 358.1 [M+H]+.

後処理

  1. customquenched with sat aq NH4Cl
  2. customSeparated
  3. extractionextracted twice more with DCM
  4. washWashed
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c928694d22ac49b184c82ab3e5c329d5
出典データセット
uspto-grants-2015_12
特許番号
US09216965B2

反応ノート

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