Water → HCID 10615550, compound

HRID 724965Notes

Reaction equation

HRID 724965 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH:19]=[O:20])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.O.[BH4-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10639163HCID 10639163, compound

Product 1

HCID 10615550HCID 10615550, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-chloro-5,11-dihydro-11-ethyl-8-formyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.5822 g, 1.84 mmol) in tetrahydrofuran (20 mL) was added water (0.1 mL) followed by sodium borohydride (0.0695 g, 1.84 mmol). The mixture was stirred for 0.5 hour then diluted with brine (20 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried, concentrated and the residue was purified by flash chromatography (gradient hexanes to ethyl acetate to yield the title compound (0.52 g, 89%), m.p. 166°-168° C.

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. customThe combined organics were dried
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography (gradient hexanes to ethyl acetate

Sources & evidence

ORD record
ord-7ab6848ad8ee4e20994a0c67084c7f21
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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