Sodium borohydride → HCID 58767572, compound

HRID 1710457Notes

Reaction equation

HRID 1710457 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:20]([C:23]#[N:24])([CH3:22])[CH3:21])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=2)=O)C.[BH4-].[Na+]>CO.C1COCC1>[CH2:18]([O:17][C:15]([C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:6]3[C:4](=[O:3])[NH:24][CH2:23][C:20]([CH3:22])([CH3:21])[N:7]3[C:8]=2[CH:9]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58767566HCID 58767566, compound

Product 1

HCID 58767572HCID 58767572, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(Cyano-dimethyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester (238, 0.725 mmol) was suspended in 3 mL of MeOH and 2 mL of THF, and 188 mg (1.45 mmol) of CoCl2 was added. While the mixture was stirred in a 0° C. bath, 274 mg (7.25 mmol) of NaBH4 was carefully added in small portions. The cold bath was removed and the mixture was stirred for 30 min. The vessel was sealed and heated to 60° C. with stirring for 4 h. The mixture was cooled and partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was then washed with 1 M NaHSO4 and brine, dried with Na2SO4, filtered, and concentrated. The residue was chromatographed (1-5% MeOH in CH2Cl2) to provided 65 mg of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid ethyl ester. ESI-MS m/z 287 [M+H]+.

Workup

  1. customThe cold bath was removed
  2. stirringthe mixture was stirred for 30 min
  3. customThe vessel was sealed
  4. temperatureheated to 60° C.
  5. stirringwith stirring for 4 h
  6. temperatureThe mixture was cooled
  7. custompartitioned between EtOAc and saturated aqueous NaHCO3
  8. washThe organic phase was then washed with 1 M NaHSO4 and brine
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed (1-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5683c0808aa247628d17f814a2387428
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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