Aluminium lithium hydride → HCID 66936512, compound

HRID 1366591Notes

Reaction equation

HRID 1366591 reaction equation
[CH3:1][C:2]1([CH3:20])[N:6]([CH3:7])[CH2:5][CH:4]2[C:8](=O)[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10](=O)[CH:3]12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1([CH3:20])[C@@H:3]2[CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C@@H:4]2[CH2:5][N:6]1[CH3:7]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66936630HCID 66936630, compound

Product 1

HCID 66936512HCID 66936512, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4,4,5-Trimethyl-2-(phenylmethyl)tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (5.39 g, 20 mmol) (Bull. Chem. Soc. Jpn., 1987, 60, 4079-4089) was dissolved in THF (50 mL) and cooled to 0° C. LiAlH4 (2.25 g, 59 mmol) was added portionwise and the resulting mixture was refluxed overnight. Upon cooling to 0° C., the reaction was quenched by the addition of water (2.25 mL), followed by 15% (w/w) NaOH (aq) (2.25 mL) and another portion of water (6.75 mL). The quenched reaction was stirred and then filtered through Celite, before being concentrated under reduced pressure. Purification by RP-HPLC yielded (rac)-cis-1,1,2-trimethyl-5-(phenylmethyl)octahydropyrrolo[3,4-c]pyrrole (1.44 g, 30%). LCMS: (M+H)+: 245.2.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. temperatureUpon cooling to 0° C.
  3. customthe reaction was quenched by the addition of water (2.25 mL)
  4. customThe quenched reaction
  5. filtrationfiltered through Celite
  6. concentrationbefore being concentrated under reduced pressure
  7. customPurification by RP-HPLC

Sources & evidence

ORD record
ord-27bb182e613c4ff49568b86ed990d5a5
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…