Sodium borohydride → tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-hydroxypropyl)picolinate

HRID 1518394ノート

反応式

HRID 1518394 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([CH2:36][CH2:37][CH:38]=[O:39])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].[BH4-].[Na+]>C1COCC1.CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[C:26]([CH2:36][CH2:37][CH2:38][OH:39])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 59447662tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-oxopropyl)picolinate

生成物 1

HCID 59447685tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-hydroxypropyl)picolinate収率 93%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 96B (5.5 g, 10.14 mmol) in THF (100 mL) and methanol (20 mL) was treated NaBH4 (0.767 g, 20.28 mmol). The reaction mixture was heated under reflux for 1 hour. The solvents were removed under vacuum. The residue was re-dissolved in EtOAc and treated with water. The organic layer was separated, and the aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography to give 5.13 g of the title compound 96C (93%): APCI (+)LC/MS: 545 (M+H)+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvents were removed under vacuum
  4. dissolutionThe residue was re-dissolved in EtOAc
  5. additiontreated with water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with additional EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d007010ed45e47f093f662be2c445191
出典データセット
uspto-grants-2012_07
特許番号
US08232273B2

反応ノート

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