Aluminium lithium hydride → 7-Hydroxymethyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 1594593Notes

Reaction equation

HRID 1594593 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[CH2:27][N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18](=O)[CH:13]2[CH2:12]1)=O>C1COCC1>[OH:8][CH2:9][CH:11]1[CH2:27][N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][CH:13]2[CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 217064047-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one

Product 1

HCID 217063797-Hydroxymethyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A three-neck flask fitted with a reflux condenser and dropping funnel was charged with 100 mL of dry THF and 2.4 g (63 mmol) of lithium aluminum hydride (LAH), and a solution of 6.0 g (21 mmol) of (7SR,8aSR)-7-methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one (Preparation 9) in 60 mL of dry THF was placed in the dropping funnel. The LAH suspension was heated to reflux and the ester solution was added over a 30-60 minutes period. Reflux continued for another 4 hours, the reaction was cooled in an ice bath and quenched by careful addition of 2.4 mL of water, 2.4 mL of 15% sodium hydroxide, and 7.2 mL of water. Stirring continued until a white precipitate formed, the mixture was filtered through Celite, and the filtrate was evaporated to give 5.0 g (97%) of the title compound of sufficient purity for use in subsequent reactions. 13C NMR (CDCl3): δ 31.1, 37.2, 51.3, 52.6, 57.4, 62.8, 62.9, 67.4, 127.0, 128.2, 129.2, 138.2. HRMS calc'd for C15H23N2O (MH+) 247.1810, found: 247.1800.

Workup

  1. customA three-neck flask fitted with a reflux condenser
  2. temperatureto reflux
  3. temperatureReflux
  4. temperaturethe reaction was cooled in an ice bath
  5. customquenched by careful addition of 2.4 mL of water, 2.4 mL of 15% sodium hydroxide, and 7.2 mL of water
  6. customformed
  7. filtrationthe mixture was filtered through Celite
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-09d1352419364493b8336a1c63aaea4d
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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