Sodium Hydroxide → HCID 69463854, compound

HRID 1791982Notes

Reaction equation

HRID 1791982 reaction equation
[CH2:1]([O:3][CH:4]([O:20][CH2:21][CH3:22])[C:5]1([C@H:8]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9]#[N:10])[CH2:7][CH2:6]1)[CH3:2].[OH-].[Na+].[H][H]>C(O)C.[Ni]>[NH2:10][CH2:9][C@@H:8]([NH:11][C@H:12]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:13])[C:5]1([CH:4]([O:3][CH2:1][CH3:2])[O:20][CH2:21][CH3:22])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11779701HCID 11779701, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69463854HCID 69463854, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In ethanol (9.0 ml) was dissolved (2S)-2-[1-(diethoxymethyl)cyclopropyl]-2-{[(1S)-1-phenylethyl]amino}acetonitrile (150 mg, 0.496 mmol). To the resulting solution were added a 5 mol/l aqueous solution of sodium hydroxide (0.5 ml, 2.5 mmol) and Raney-nickel (R-100, 1.5 g) were added and the mixture was stirred at room temperature for 5 hours in a hydrogen gas stream. The catalyst was filtered off and the residue was washed with ethanol. The filtrate was concentrated under reduced pressure. Water and chloroform were added to the residue for separation. The organic layer was dried over sodium sulfate, filtered, and then evaporated under reduced pressure, whereby the title compound (150 mg, 98.4%) was obtained as a slightly yellow oil.

Workup

  1. additionwere added
  2. filtrationThe catalyst was filtered off
  3. washthe residue was washed with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionWater and chloroform were added to the residue for separation
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure, whereby the title compound (150 mg, 98.4%)
  9. customwas obtained as a slightly yellow oil

Sources & evidence

ORD record
ord-f8d526ce1ebf43a795ddc514a8c2c217
Source dataset
uspto-grants-2006_07
Patent number
US07074837B2

Reaction notes

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