Tetrahydrofuran → HCID 20682341, compound

HRID 1594586Notes

Reaction equation

HRID 1594586 reaction equation
CO[C:3]([C:5]1([CH3:22])[CH2:21][N:8]2[CH2:9][CH:10](C)[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=O)[CH:7]2[CH2:6]1)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:29]1COCC1>>[OH:4][CH2:3][C:5]1([CH3:22])[CH2:21][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:29]=3)[CH2:12][CH:7]2[CH2:6]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 70245908HCID 70245908, compound

Product 1

HCID 20682341HCID 20682341, compoundYield 58%

Procedure

A solution of 3.33 g (11 mmol) of (7RS,8aSR)-7-methoxycarbonyl-7-methyl-2-phenyl-methyl-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 hours 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 minutes, 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 minutes
  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-787f94c1eb1748149811555f4e2c6518
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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