Water → HCID 57129670, compound

HRID 581220Notes

Reaction equation

HRID 581220 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:8]2[CH2:14][CH:13]3[N:15]([C:16](OC(C)(C)C)=O)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:8]2[CH2:9][CH:10]3[N:15]([CH3:16])[CH:13]([CH2:12][CH2:11]3)[CH2:14]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 57268474HCID 57268474, compound

Product 1

HCID 57129670HCID 57129670, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(5-Amino-2-methoxyphenyl)-8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]octane (D4, 0.385 g, 1.16 mmol) was dissolved in dry THF (30 ml) with stirring and was treated with lithium aluminium hydride (0.088 g, 2.32 mmol) under argon. The reaction mixture was then heated to reflux. After 2 h and 4 h, further amounts of lithium aluminium hydride (0.132 g, 3.48 mmol) were added. Reflux was then maintained for a further 4 h, before the reaction mixture was allowed to cool. Water (0.352 ml) was then added, followed by 10% NaOH (0.528 ml) and water (0.880 ml). The mixture was then stirred for 0.5 h before being filtered through kieselguhr. The filter pad was then washed with THF (20 ml) and the filtrate evaporated under reduced pressure to give the title compound as a brown solid (0.242 g, 85%).

Workup

  1. temperatureThe reaction mixture was then heated to reflux
  2. temperatureReflux
  3. temperaturewas then maintained for a further 4 h, before the reaction mixture
  4. temperatureto cool
  5. stirringThe mixture was then stirred for 0.5 h
  6. filtrationbefore being filtered through kieselguhr
  7. washThe filter pad was then washed with THF (20 ml)
  8. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8a4a9c22770440793a6978648ec2974
Source dataset
uspto-grants-1999_07
Patent number
US05919932

Reaction notes

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