HCID 11013639, compound → HCID 67777569, compound

HRID 2065778Notes

Reaction equation

HRID 2065778 reaction equation
[CH2:1]([N:8]([C@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:20])[C@@H:9]([CH3:18])[CH2:10][C:11](OC(C)(C)C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)C>[CH2:1]([N:8]([C@H:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:20])[C@@H:9]([CH3:18])[CH2:10][CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11013639HCID 11013639, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 67777569HCID 67777569, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl (3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]butanoate (24 g, 67.9 mmol) is dissolved in anhydrous THF (237 mL) and cooled to 0° C. under an argon atmosphere. 1 M Lithium aluminum hydride in THF (237 mL, 237 mmol) is added dropwise over 10 min. The reaction mixture is stirred at 0° C. for 1 h and then at 60° C. for 1 h. The mixture is cooled to room temperature (RT) and diluted with diethyl ether (500 mL). The reaction is quenched with a mixture of CELITE® and Na2SO4.10 H2O (1:1) is added portionwise over 15 min. The mixture is filtered and concentrated under a vacuum to afford the title compound as a colorless oil (17.54 g, 90%). LC-ES/MS m/z 284 (M+1).

Workup

  1. waitat 60° C. for 1 h
  2. temperatureThe mixture is cooled to room temperature (RT)
  3. customThe reaction is quenched with a mixture of CELITE® and Na2SO4
  4. addition10 H2O (1:1) is added portionwise over 15 min
  5. filtrationThe mixture is filtered
  6. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-ad65cddfb86f44c999c8e0f14bd1f65f
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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