Lithium aluminum hydride → HCID 19694419, compound

HRID 557930Notes

Reaction equation

HRID 557930 reaction equation
[AlH4-].[Li+].[CH2:3]([N:10]1[CH2:14][CH:13]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[O:21][C:22](=[O:23])[CH:12]2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:3]([N:10]1[CH2:11][CH:12]([CH2:22][OH:23])[CH:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[OH:21])[CH2:14]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 3309019HCID 3309019, compound

Product 1

HCID 19694419HCID 19694419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium tetrahydroaluminate in tetrahydrofuran (1.00 M, 1.50 mL) was added to a solution of 2-benzyl-2,3,3a,9b-tetrahydrochromeno[3,4-c]pyrrol-4(1H)-one (188.0 mg, 0.0006730 mol) in THF (2.0 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and then quenched with acetone. Ethyl acetate (10 mL) was added and the resulting mixture was treated with NaOH (1N, 3 mL) and then was filtered through a pad of celite. The filtrate was washed with brine (2×5 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product.

Workup

  1. customquenched with acetone
  2. additionEthyl acetate (10 mL) was added
  3. additionthe resulting mixture was treated with NaOH (1N, 3 mL)
  4. filtrationwas filtered through a pad of celite
  5. washThe filtrate was washed with brine (2×5 mL)
  6. dry with materialthe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e90d203ece24ae59bad3e459267ae76
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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