Hydrochloric Acid → HCID 57020529, compound

HRID 259905Notes

Reaction equation

HRID 259905 reaction equation
[CH2:1]([N:8]([C@H:16]([C:24](=[O:38])[CH2:25][C@@H:26]([NH:34][C:35](=[O:37])[CH3:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH2:1]([N:8]([C@H:16]([C@@H:24]([OH:38])[CH2:25][C@@H:26]([NH:34][C:35](=[O:37])[CH3:36])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10874813HCID 10874813, compound

Product 1

HCID 57020529HCID 57020529, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,5S)-2-(N,N-Dibenzylamino)-5-acetylamino-1,6-diphenyl-3-hexanone (3.0 g, 5.944 mmol) was dissolved in methanol (15 ml). Sodium borohydride (1.80 g, 23.78 mmol) was slowly added to the resultant solution while chilling with ice water so as not to raise the temperature above 10° C., thereby conducting reaction. The reaction mixture was stirred at room temperature for 5 hours. To the reaction mixture, was added a 10% hydrochloric acid (10 ml) while chilling with ice water. After bubbling ceased, the mixture was extracted with ethyl acetate (50 ml). The extract was washed with an aqueous sodium chloride and dried over sodium sulfate. The solvent was distilled off, and the resulting crude product was recrystallized from a mixed solvent of ethyl acetate (1.5 ml) and n-hexane (6 ml), thereby obtaining the title compound (2.70 g, 86.1%) as colorless crystals.

Workup

  1. temperatureto raise the temperature above 10° C.
  2. customreaction
  3. customAfter bubbling
  4. extractionthe mixture was extracted with ethyl acetate (50 ml)
  5. washThe extract was washed with an aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe resulting crude product was recrystallized from a mixed solvent of ethyl acetate (1.5 ml) and n-hexane (6 ml)

Sources & evidence

ORD record
ord-8d743006f7cd44e1be436e1ea203d258
Source dataset
uspto-grants-1996_06
Patent number
US05523458

Reaction notes

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