Ammonium Chloride → HCID 21699661, compound

HRID 1597281Notes

Reaction equation

HRID 1597281 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([C:22](OC)=[O:23])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[Cl-].[NH4+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([CH2:22][OH:23])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 21699687HCID 21699687, compound

Product 1

HCID 21699661HCID 21699661, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Methyl 2-t-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine-10-carboxylate (1.14 g, 3.05 mmol) was dissolved in ethanol (3 ml), followed by adding thereto sodium tetrahydroborate (138.4 mg, 3.66 mmol) and then a solution of calcium chloride (338.5 mg, 3.05 mmol) in ethanol (3 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 4 hours and then at 60° C. for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the desired compound (442 mg, 46%) as a yellow oil.

Workup

  1. additionby adding
  2. waitat 60° C. for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-846acf802b8b4c74bfdca168b2a402ff
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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