Sodium Hydroxide → HCID 69057496, compound

HRID 2100620Notes

Reaction equation

HRID 2100620 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13]C)[C:10]2[C:9](=[O:15])[NH:8][C@H:7]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2].C(C1C=C(OC)C2C(=O)N[C@@H]3CN(C(OC(C)(C)C)=O)C[C@H]3C=2C=1)C.B(Br)(Br)Br.[OH-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.Cl>[CH2:1]([C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[C:9](=[O:15])[NH:8][C@H:7]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:18][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 90495Di-tert-butyl dicarbonateHCID 69054977HCID 69054977, compoundHCID 69059200HCID 69059200, compound

Product 1

HCID 69057496HCID 69057496, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3aR,9bS)-tert-butyl 8-ethyl-6-methoxy-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Example 51, Part B (686 mg, 1.98 mmol) in 100 mL of methylene chloride was added boron tribromide (2.38 mL of a 1 M solution in methylene chloride, 2.38 mmol) dropwise at ambient temperature. The solution was allowed to stir for 8 h and then there was added 100 mL of 1 N sodium hydroxide followed by followed by di-tert-butyl dicarbonate (648 mg, 2.97 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction was diluted with 1 N HCl to give a pH of −5-6. The layers were separated and the organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified (ISCO, elution with 0-50% EtOAc/hexane) to afford 413 mg (63%) of the title compound as a white solid. LRMS (ESI): 333.2 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 18 h
  2. customto give a pH of −5-6
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified
  8. wash(ISCO, elution with 0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-9a43d15badb446c69bc0080a6d98ba70
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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