Acetone → HCID 19774271, compound

HRID 1613654Notes

Reaction equation

HRID 1613654 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:26]=[CH:25][C:19]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:18][CH:17]=1.[BH4-].[Na+].CC(C)=O>CO>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 19774262HCID 19774262, compound

Product 1

HCID 19774271HCID 19774271, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (XXI) (0.75 g) was combined with NaBH4 (0.14 g) in MeOH (30 ml) and stirred at ambient temperature for 31/2 hours. A further 0.14 g NaBH4 was added and the reaction was stirred a further 1/2 hour. Acetone (10 ml) was added. After stirring 18 hours, the solvent was evaporated and the residue was partitioned between EtOAc and aqueous NaHCO3. The EtOAc was evaporated, and the residue was chromatographed on a silica column, eluting the product with CH2Cl2 /MeOH as a gummy solid (0.5 g). This was converted to its HCl salt using EtOH/concentrated HCl and recrystallized from EtOH to yield Compound XXII.HCl (0.2 g), m.p. 214°-220° (dec.). The elemental analysis for C, H, and N and mass spectra were consistent with the structure indicated. The NMR spectrum suggested that the 1,2-trans-isomer was the principal constituent, though some of the 1,2-cis-isomer was present also.

Workup

  1. stirringthe reaction was stirred a further 1/2 hour
  2. stirringAfter stirring 18 hours
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between EtOAc and aqueous NaHCO3
  5. customThe EtOAc was evaporated
  6. customthe residue was chromatographed on a silica column
  7. washeluting the product with CH2Cl2 /MeOH as a gummy solid (0.5 g)
  8. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-dd97fb4a6341488982c62c1b1cb3ee60
Source dataset
uspto-grants-1993_03
Patent number
US05194450

Reaction notes

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