Ammonium Chloride → HCID 10215337, compound

HRID 723392Notes

Reaction equation

HRID 723392 reaction equation
[OH:1][C@H:2]1[C:11](=[O:12])[C:10]2[CH:9]=[CH:8][N:7]3[C:13]([CH3:19])=[C:14]([CH2:16][O:17][CH3:18])[N:15]=[C:6]3[C:5]=2[NH:4][C@@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:12][C@@H:11]1[C:10]2[CH:9]=[CH:8][N:7]3[C:13]([CH3:19])=[C:14]([CH2:16][O:17][CH3:18])[N:15]=[C:6]3[C:5]=2[NH:4][C@H:3]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:2]1[OH:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69586067HCID 69586067, compound

Product 1

HCID 10215337HCID 10215337, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.0 g of (8R,9R)-8-hydroxy-2-methoxymethyl-3-methyl-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridin-7-one are suspended in 40 ml methanol and 0.6 g sodium borohydride are added in small portions over a period of 30 min. After 1 h at ambient temperature the reaction mixture is poured onto of 60 ml icewater and 2 g ammonium chloride. The organic layer is separated and the aqueous phase extracted three times with dichloromethane. The combined organic phases are dried over anhydrous sodium sulfate and the solvent removed in vacua. The residue is purified by column chromatography on silica gel (eluent: dichloromethane/methanol 100:1). Crystallization from diethyl ether yields 4.7 g (78%) of the title compound as a light brown solid (BYK237362, m.p. 102–104° C.).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous phase extracted three times with dichloromethane
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulfate
  4. customthe solvent removed in vacua
  5. customThe residue is purified by column chromatography on silica gel (eluent: dichloromethane/methanol 100:1)
  6. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-b5fcba61a2064151a806609d6bdca239
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

Loading…