Aluminium lithium hydride → HCID 45095245, compound

HRID 585818Notes

Reaction equation

HRID 585818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:17]2[N:16]3[C@H:18]([CH3:23])[CH2:19][NH:20][C:21](=O)[C@@H:15]3[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:8]>O1CCCC1>[CH2:7]([C:9]1[C:17]2[N:16]3[C@H:18]([CH3:23])[CH2:19][NH:20][CH2:21][C@@H:15]3[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69414650HCID 69414650, compound

Product 1

HCID 45095245HCID 45095245, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (37 mg, 0.97 mmol) was added to a solution of (4R,10aS)-6-ethyl-4-methyl-3,4,10,10a-tetrahydro-2H-pyrazino[1,2-a]indol-1-one (56 mg, 0.24 mmol) in tetrahydrofuran (3 mL) and the resulting suspension was heated to reflux for 1 h. After cooling the reaction was quenched by careful addition of 1 M aqueous sodium potassium tartrate solution (5 mL). Then methanol (5 mL) and ethyl acetate (5 mL) were added, the organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography on 20 g SiO2 (CH2Cl2/MeOH/NH4OH 95:5:0.1) yielded the title compound (20 mg, 38%). White solid. ISP-MS: m/e=217.3 ([M+H]+).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling the reaction
  4. customwas quenched by careful addition of 1 M aqueous sodium potassium tartrate solution (5 mL)
  5. additionThen methanol (5 mL) and ethyl acetate (5 mL) were added
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-593b98dfefdf4c2d9a3ae24bd2c22e9b
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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