HCID 131727755, compound → HCID 131727756, compound

HRID 1435929Notes

Reaction equation

HRID 1435929 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=O)[C@@H:9]3[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[C:12]2[NH:11][CH2:10][C@@H:9]3[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 131727755HCID 131727755, compound

Product 1

HCID 131727756HCID 131727756, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (±)-cis tert-butyl 6-methoxy-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate (1.4 g, 4.5 mmol) in 30 mL of THF at 0° C. was added borane THF complex (20 mL of a 1 M solution in THF, 20 mmol) dropwise. The reaction was allowed to warm to ambient temperature and was stirred for 2 h. The reaction was quenched carefully with water and extracted with ethyl acetate. The organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 1.26 g (92%) of the title compound. 1H NMR (CDCl3) (some signals doubled due to rotamers): δ 6.68-6.55 (overlapping m, 3H), 4.42 (broad s, 1H), 3.95-3.82 (m, 1H), 3.78 (s, 3H), 3.64-3.55 (m, 1H), 3.38-3.15 (overlapping m, 4H), 3.02-2.92 (m, 1H), 2.52-2.42 (m, 1H), 3.63 and 3.61 (s, 9H).

Workup

  1. customThe reaction was quenched carefully with water
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b6eaf701a16b4803aa1422ec1453c80a
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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