Benzylamine → HCID 70008795, compound

HRID 1267900Notes

Reaction equation

HRID 1267900 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10](=O)[C@@H:11]([F:23])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:31]([NH:38][C@H:10]1[C@@H:11]([F:23])[CH2:12][C@@H:13]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@:9]1([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:15][C@H:14]2[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 70008248(1R*,3S*,5S*,6R*)-8-Benzyl-3-fluoro-1-phenyl-6-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octan-2-one

Product 1

HCID 70008795HCID 70008795, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(1R*,3S*,5S*,6R*)-8-Benzyl-3-fluoro-1-phenyl-6-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octan-2-one (Description 36a; 1.68 g, 4.1 mmol), titanium iso-propoxide (1.8 mL, 6.2 mmol) and benzylamine (520 μL, 4.7 mmol) were heated together at 85° C. for two hours, then cooled and diluted with methanol (30 mL). The solution was then heated to 50° C. and sodium borohydride (1.06 g, 28 mmol) was added portionwise over 4 hours. After addition was complete, the solution was heated for a further 16 hours, then cooled and poured into aqueous sodium hydroxide solution (100 mL, 1M). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts were dried (MgSO4). Concentration in vacuo gave a gum which was purified by silica chromatography to give the title compound (651 mg, 1.3 mmol).

Workup

  1. temperaturecooled
  2. additionAfter addition
  3. temperaturethe solution was heated for a further 16 hours
  4. temperaturecooled
  5. customThe suspension formed
  6. extractionwas extracted with ethyl acetate (2×100 mL)
  7. dry with materialthe extracts were dried (MgSO4)
  8. concentrationConcentration in vacuo
  9. customgave a gum which
  10. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-73ef5466dc964c72bd8dcaf5aa5aa632
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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