Hydrochloric Acid → HCID 20087845, compound

HRID 275345Notes

Reaction equation

HRID 275345 reaction equation
[N+:1]([C:4]12[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5]2)([O-:3])=[O:2].[BH4-].[Na+].CCOCC.[ClH:22]>CO>[ClH:22].[OH:14][CH:13]1[C:4]2([N+:1]([O-:3])=[O:2])[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 13108572HCID 13108572, compound

Product 1

HCID 20087845HCID 20087845, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8a-nitrodecahydronapthalen-1-one [P. Dampawan and W. W. Zajac Jr. Synthesis, 545, 1983] (1.2 g, 6.1 mmol) in MeOH (10 ml) at 0° C., add sodium borohydride (0.09 g) and warm to RT. After 0.5 hr, add ether and 1N HCl. Dry and concentrate the organic layer. Dissolve the residue in EtOH (50 ml) and add this to Raney Nickel (1.2 g, wet weight) and place under 60 psi of H2 at 55° C. After 24 hr., filter though celite and concentrate to dryness. Dissolve the resultant oil in Et2O add dry HCl in MeOH and collect the title compound as a colorless precipitate EI MS: M+=169.

Workup

  1. customDry
  2. concentrationconcentrate the organic layer
  3. dissolutionDissolve the residue in EtOH (50 ml)
  4. additionadd this to Raney Nickel (1.2 g, wet weight) and place under 60 psi of H2 at 55° C
  5. waitAfter 24 hr
  6. filtration, filter though celite
  7. concentrationconcentrate to dryness
  8. dissolutionDissolve the resultant oil in Et2O
  9. additionadd dry HCl in MeOH
  10. customcollect the title compound as a colorless precipitate EI MS

Sources & evidence

ORD record
ord-bcada07fb2c74a02bf0334e6801e167b
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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