Sodium borohydride → (7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridine

HRID 2249709Notes

Reaction equation

HRID 2249709 reaction equation
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C:7](=[O:19])[C@H:6]([OH:20])[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([OH:19])[C@H:6]([OH:20])[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69290336(8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 69288589(7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g (0.6 mmol) of (8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one is dissolved in 15 ml of methanol and admixed with 40 mg (1.1 mmol) of sodium borohydride in portions with ice cooling. After 10 min, hydrolysis is effected using saturated sodium hydrogencarbonate solution and extraction using dichloromethane. The organic phase is dried over magnesium sulphate and evaporated. The residue is crystallized using diethyl ether. 0.16 g (80%) of the title compound is isolated as a colourless solid (m.p. 260-261° C.).

Workup

  1. customhydrolysis
  2. extractionsodium hydrogencarbonate solution and extraction
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is crystallized

Sources & evidence

ORD record
ord-ea8179929f6e4adeb9b2132219a183d9
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

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