HCID 11725636, compound → HCID 66672777, compound

HRID 2091655Notes

Reaction equation

HRID 2091655 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.CCOCC>[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 11725636HCID 11725636, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 66672777HCID 66672777, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}butanoate (6.2 g, 17.6 mmol) was dissolved in THF (100 mL). The 1 L-flask was purged with N2 and cooled to 0° C. Lithium aluminum hydride (2.7 g, 69.8 mmol) was slowly added over 5 minutes. The reaction was allowed to stir at 0° C. for 1 hour, and then heated to 60° C. for 1 hour. The reaction was cooled to room temperature and diluted with Et2O (500 mL). This solution was quenched with a mixture of celite:Na2SO410H2O (1:1) added over 15 minutes. The solution was then filtered and the mother liquor condensed to yield 3.9 g (13.8 mmol, 78%) of the title compound.

Workup

  1. customThe 1 L-flask was purged with N2
  2. temperatureheated to 60° C. for 1 hour
  3. temperatureThe reaction was cooled to room temperature
  4. customThis solution was quenched with a mixture of celite
  5. additionNa2SO410H2O (1:1) added over 15 minutes
  6. filtrationThe solution was then filtered
  7. customthe mother liquor condensed

Sources & evidence

ORD record
ord-91fe2d03fdbc40d5ab172f23f509aa8f
Source dataset
uspto-grants-2013_05
Patent number
US08440661B2

Reaction notes

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