Water → HCID 69054150, compound

HRID 2100582Notes

Reaction equation

HRID 2100582 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][N:5]1[C@H:14]2[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:25]([F:28])([F:27])[F:26])[C:7]=2[C:6]1=[O:29].O.[OH-].[Li+]>C1COCC1>[C:21]([O:20][C:18]([N:16]1[CH2:17][C@H:13]2[C@@H:14]([N:5]([CH2:4][C:3]([OH:30])=[O:2])[C:6](=[O:29])[C:7]3[C:8]([C:25]([F:27])([F:26])[F:28])=[CH:9][CH:10]=[CH:11][C:12]=32)[CH2:15]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 69054924HCID 69054924, compound

Product 1

HCID 69054150HCID 69054150, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3aR,9bS)-tert-butyl 4-(2-methoxy-2-oxoethyl)-5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 18, Part A (105 mg, 0.25 mmol) in 4 mL of THF and 2 mL of water was added lithium hydroxide (12 mg, 0.49 mmol). The resulting mixture was allowed to stir at ambient temperature for 2 h. The reaction was quenched with 10 mL of 1N HCl and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated in vacuo to afford 100 mg (98%) of the title compound. LRMS (ESI): 415.20 (M+H)+.

Workup

  1. customThe reaction was quenched with 10 mL of 1N HCl
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19bb596e395c4d12b0a66180bb9331ad
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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