Water → HCID 59657524, compound

HRID 1866027Notes

Reaction equation

HRID 1866027 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19](=[O:24])C(F)(F)F)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[OH2:29]>CN(C)C=O.COC(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19]([OH:24])=[O:29])=[C:10]2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 59657577HCID 59657577, compound

Product 1

HCID 59657524HCID 59657524, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 0.29 g (0.77 mmol) 10-(2,2,2-trifluoro-acetyl)-3,4-dihydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester in 7 ml N,N-dimethylformamide were subsequently added 0.22 g (4.6 mmol) sodium hydride (50% in oil) and a solution of 0.070 ml (3.9 mmol) water in 1 ml N,N-dimethylformamide at room temperature. The reaction mixture was diluted with tert-butyl methyl ether after 2 h and extracted with 1 M sodium hydroxide solution (2×30 ml). The combined aqueous layers were acidified (pH 1-2) with 2 M hydrochloric acid at 0° C. and extracted with tert-butyl methyl ether (3×50 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.21 g, 86%) as a light brown solid.

Workup

  1. customat room temperature
  2. extractionextracted with 1 M sodium hydroxide solution (2×30 ml)
  3. customat 0° C.
  4. extractionextracted with tert-butyl methyl ether (3×50 ml)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-458e8c7c89d0412cae888b3c36d68a40
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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