Benzyl Bromide → HCID 69052907, compound

HRID 2100626Notes

Reaction equation

HRID 2100626 reaction equation
CCCCCC.[H-].[Na+].[CH2:9]([C:11]1[CH:20]=[C:19]([CH3:21])[C:18]2[C:17](=[O:22])[NH:16][C@@H:15]3[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C@H:14]3[C:13]=2[CH:12]=1)[CH3:10].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[CH2:33]([N:16]1[C@@H:15]2[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:25][C@H:14]2[C:13]2[CH:12]=[C:11]([CH2:9][CH3:10])[CH:20]=[C:19]([CH3:21])[C:18]=2[C:17]1=[O:22])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 69055271HCID 69055271, compound

Product 1

HCID 69052907HCID 69052907, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hexane-washed sodium hydride (6 mg of 60% dispersion in mineral oil, 0.15 mmol) in 1 mL 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 (25 mg, 0.076 mmol) in 2 mL of THF. The mixture was stirred at ambient temperature for 30 min, at which time gas evolution had ceased. Then there was added benzyl bromide (0.027 mL, 0.23 mmol) and the resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was quenched with 1N HCl and diluted with ethyl acetate. The organics were washed sequentially with sat'd aq. NaHCO3, and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 4:1 hexane/EtOAc) to afford 28 mg (88%) of the title compound as an oil. LRMS (ESI): 421.1 (M+H)+.

Workup

  1. stirringto stir at ambient temperature for 18 h
  2. customThe reaction was quenched with 1N HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed sequentially with sat'd aq. NaHCO3, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (elution with 4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-f565a978e29d4ad69856090bb9210763
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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