N-Acetyl-L-leucine → (1S)-5-tert-butyl-2,3-dihydro-1H-inden-1-amine

HRID 451598

Reaction equation

HRID 451598 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH2:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].C(N[C@H](C(O)=O)CC(C)C)(=O)C>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@@H:10]([NH2:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70912N-Acetyl-L-leucineHCID 115066015-tert-butyl-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 24777891(1S)-5-tert-butyl-2,3-dihydro-1H-inden-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

5-tert-Butyl-2,3-dihydro-1H-inden-1-ylamine (25.51 g, 93% potency), N-acetyl-(L)-leucine (23.34 g), and methanol (315 mL) were combined and heated at 65° C. for 1 hour. The solution was allowed to cool to ambient temperature. The solids were filtered and washed with toluene. The solid was then resuspended in methanol (125 mL) and brought to reflux. The solution was allowed to cool to ambient temperature and the solids were filtered. The solid was dried at 40° C. under reduced pressure to provide the title compound (98.7% ee).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe solids were filtered
  3. washwashed with toluene
  4. temperatureto reflux
  5. temperatureto cool to ambient temperature
  6. filtrationthe solids were filtered
  7. customThe solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-cbdd40558afe41ffaa64d1cb2a577c28
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Linked notes

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