Aluminium lithium hydride → HCID 69055105, compound

HRID 2100638Notes

Reaction equation

HRID 2100638 reaction equation
[CH2:1]([N:8]1[CH2:20][C@@H:19]2[C@H:10]([NH:11][C:12](=O)[C:13]3[C:14]([CH3:21])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:20][C@@H:19]2[C@H:10]([NH:11][CH2:12][C:13]3[C:14]([CH3:21])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69054317HCID 69054317, compound

Product 1

HCID 69055105HCID 69055105, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of (±)-trans-2-benzyl-6-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one, from Example 101, Part A, (830 mg, 2.84 mmol) in 20 mL of THF was added lithium aluminum hydride (3.4 mL of a 1 M solution in THF, 3.4 mmol). The reaction was heated in a microwave oven at 100° C. for 1.5 h. The reaction was cooled, filtered through a pad of silica gel with 10% methanol/methylene chloride, and concentrated in vacuo. The residue was purified (ISCO, elution with 0-12% methanol/methylene chloride) to afford 345 mg (44%) of the title compound as a solid. 1H NMR (CDCl3): δ 7.40-7.25 (m, 5H), 7.08-6.98 (m, 2H), 6.80 (d, 1H), 4.12 (ABq, 2H), 3.87 (ABq, 2H), 3.42-3.37 (m, 1H), 3.15-3.06 (m, 2H), 2.98-2.90 (m, 1H), 2.80-2.71 (m, 2H), 2.17 (s, 3H). LRMS (ESI): 279.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of silica gel with 10% methanol/methylene chloride
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. wash(ISCO, elution with 0-12% methanol/methylene chloride)

Sources & evidence

ORD record
ord-c910cf5771204869b3a71459c9882a84
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…