Acetic Acid → HCID 54394222, compound

HRID 1885740Notes

Reaction equation

HRID 1885740 reaction equation
[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:20])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH3:19])[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1.C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>O>[Cl:1][C:2]1[CH2:3][NH:4][CH2:5][C:6]2([CH3:20])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH3:19])[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 53780973HCID 53780973, compound

Product 1

HCID 54394222HCID 54394222, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1.50 g of 10-chloro-1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 14 ml of acetic acid, cooled to 15° C. under nitrogen, was added, 1.00 g of sodium cyanoborohydride, with stirring. The reaction mixture was stirred an additional 6.75 hr and water was added. The solution was made basic (pH 12) with 50% aqueous sodium hydroxide solution. The mixture was extracted with ether and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated. The residue was dissolved in 15 ml acetic acid and, as above, treated with 1.63 g of sodium cyanoborohydride for 5 hr. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-10% methanol/ether) to afford 1.04 g (69%) of product. Recrystallization from ether-dichloromethane afforded the analytical sample, mp 168°-170° C.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ether
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. dissolutionThe residue was dissolved in 15 ml acetic acid
  8. additionas above, treated with 1.63 g of sodium cyanoborohydride for 5 hr
  9. customThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-10% methanol/ether)

Sources & evidence

ORD record
ord-2e6afa569ded4f958dfb2b5508bdd5cf
Source dataset
uspto-grants-1992_09
Patent number
US05145965

Reaction notes

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