HCID 131727758, compound → HCID 131727761, compound

HRID 1435940Notes

Reaction equation

HRID 1435940 reaction equation
[CH3:1][N:2]1[C:11]2[C:10]([CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:5]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:4]2[C:3]1=O.CC1C2NC(=O)[C@@H]3CN(C(OC(C)(C)C)=O)C[C@@H]3C=2C=CC=1>C1COCC1>[CH3:1][N:2]1[C:11]2[C:10]([CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:5]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 131727758HCID 131727758, compoundHCID 131727759HCID 131727759, compound

Product 1

HCID 131727761HCID 131727761, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (±)-cis tert-butyl 5,6-dimethyl-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate, an intermediate from Example 18, Part B (0.40 g, 1.27 mmol) in 10 mL of THF at 0° C. was added borane THF complex (6.5 mL of a 1 M solution in THF, 6.5 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 0.37 g (97%) of the title compound as an oil.

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-033600aff7ec4632af1f3bb6f5250d13
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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