Aluminium lithium hydride → HCID 20682341, compound

HRID 861360Notes

Reaction equation

HRID 861360 reaction equation
C[O:2][C:3]([C:5]1([CH3:22])[CH2:21][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=O)[CH:7]2[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][C:5]1([CH3:22])[CH2:21][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][CH:7]2[CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70197772HCID 70197772, compound

Product 1

HCID 20682341HCID 20682341, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.33 g (11 mmol) of (7RS,8aSR)-7-methoxycarbonyl-7-methyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one (Jones, R. C. F.; Howard, K. J. J. Chem. Soc., Perkin Trans. 1, 1993, 2391) in 125 mL of dry THF was added dropwise to a stirred suspension of 1.26 g (33 mmol) of lithium aluminum hydride in 125 mL of dry THF. The solution was stirred for 2 h at room temperature, and carefully quenched with 1.26 mL of water, 1.26 mL of 15% NaOH, and 3.78 mL of water. After stirring for 30 min, the mixture was filtered through Celite, dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography eluting with 9:1 chloroform:methanol gave 1.67 g (58%) of the title compound. 13C NMR (base, CDCl3): δ 25.3, 39.7, 41.8, 51.1, 51.6, 57.1, 62.3, 62.9, 63.3. 71.3, 127.0, 128.2, 128.7, 129.2, 138.3. m/z (MH+) 261.

Workup

  1. customcarefully quenched with 1.26 mL of water, 1.26 mL of 15% NaOH, and 3.78 mL of water
  2. stirringAfter stirring for 30 min
  3. filtrationthe mixture was filtered through Celite
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography
  8. washeluting with 9:1 chloroform

Sources & evidence

ORD record
ord-4d61916d5983401e8ca5a7059defbe68
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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