Aluminium lithium hydride → HCID 11997228, compound

HRID 1985712Notes

Reaction equation

HRID 1985712 reaction equation
C(O[C:6]([N:8]1[CH2:20][C@@H:19]2[N:11]([C:12]3[N:13]=[C:14]4[CH2:23][O:22][CH2:21][C:15]4=[CH:16][C:17]=3[CH2:18]2)[C@H:10]([CH3:24])[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:24][C@@H:10]1[CH2:9][N:8]([CH3:6])[CH2:20][C@@H:19]2[N:11]1[C:12]1[N:13]=[C:14]3[CH2:23][O:22][CH2:21][C:15]3=[CH:16][C:17]=1[CH2:18]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67237589HCID 67237589, compound

Product 1

HCID 11997228HCID 11997228, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.100 g (5R,8aR)-5-methyl-3,5,6,8,8a,9-hexahydro-1H-2-oxa-4,4b,7-triaza-cyclopenta[b]fluorene-7-carboxylic acid tert-butyl ester and 0.040 g lithium aluminum hydride in 3 ml tetrahydrofuran was heated to reflux for 2 h. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was washed with brine evaporated and purified by chromatography on silica gel with dichloromethane:methanol:ammonia=90:10:1. to yield 0.053 g of the title compound as slightly yellow gum (MS: 246.4 (M+H+))

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. custompartitioned between water and ethyl acetate
  4. washThe organic phase was washed with brine
  5. customevaporated
  6. custompurified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-3618dbf9e7a547bbb785d4263f16056d
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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