Sodium Hydroxide → (S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propylamine

HRID 1379966Notes

Reaction equation

HRID 1379966 reaction equation
[CH3:1][NH:2][C:3](=O)[C@@H:4]([N:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>ClCCl>[CH3:1][NH:2][CH2:3][C@@H:4]([N:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 86750266(S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

Product 1

HCID 67711663(S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve (S)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide (0.31 g, 0.98 mmol) in dichloromethane (10 mL) and cool in a dry ice/acetone bath to -78° C. Add diisobutylaluminum hydride (1.96 mL, 1.5M in toluene, 2.94 mmol). Allow to warm slowly to ambient temperature and stir for 16 hours. Slowly add a 15% aqueous solution of sodium hydroxide (3.0 mL). Extract with dichloromethane, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound as a mixture which is taken on to the next step without further purification.

Workup

  1. temperatureAllow to warm slowly to ambient temperature
  2. extractionExtract with dichloromethane
  3. dry with materialdry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-58a860160cd84251ba259d3f8fcb0d57
Source dataset
uspto-grants-1997_09
Patent number
US05672602

Reaction notes

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