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

HRID 1518394Notes

Reaction equation

HRID 1518394 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d007010ed45e47f093f662be2c445191
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…