Sodium hydride → HCID 91189016, compound

HRID 2100627Notes

Reaction equation

HRID 2100627 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:11](=[O:16])[NH:10][C@@H:9]3[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C@H:8]3[C:7]=2[CH:6]=1)[CH3:4].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>C1COCC1>[CH2:3]([C:5]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:11](=[O:16])[N:10]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C@@H:9]3[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:19][C@H:8]3[C:7]=2[CH:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 69055271HCID 69055271, compound

Product 1

HCID 91189016HCID 91189016, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (33 mg of 60% dispersion in mineral oil, hexane-washed, 0.87 mmol) in 4 mL of THF was added (±)-trans-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 74, Part A (191 mg, 0.58 mmol) in 10 mL of THF. The resulting mixture was stirred at ambient temperature for 30 min, at which time gas evolution has ceased. Then there was added methyl bromoacetate (0.082 mL, 0.87 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction was quenched with 10 mL of 1 N HCl and extracted with ethyl acetate. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 15-25% EtOAc/hexane) to afford 180 mg (77%) of the title compound. LRMS (ESI): 403.1 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 18 h
  2. customThe reaction was quenched with 10 mL of 1 N HCl
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with sat'd aq NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (elution with 15-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-0f7c55ab24f040b8bf47fd6ad9839b3e
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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