HCID 11287627, compound → HCID 9855879, compound

HRID 585819Notes

Reaction equation

HRID 585819 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:15]3=[CH: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:15]3=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

4

Reactant 2

HCID 11287627HCID 11287627, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9855879HCID 9855879, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (532 mg) was added in portions to a solution of (R)-6-ethyl-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (800 mg, 3.50 mmol) in tetrahydrofuran (30 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 (50 mL). Then methanol (50 mL) and ethyl acetate (50 mL) were added, the organic layer was separated, washed with brine, dried (MgSO4), and evaporated to yield the title compound (750 mg, 100%). White solid. ISP-MS: m/e=215.3 ([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 (50 mL)
  5. additionThen methanol (50 mL) and ethyl acetate (50 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-3e1defbf1e7642ac8a8bc6827b4f02ea
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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