N-Acetyl-D-leucine → (1R)-5-(1,1-Dimethylethyl)-2,3-dihydro-1H-inden-1-amine

HRID 2223393

Reaction equation

HRID 2223393 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 1241420N-Acetyl-D-leucineHCID 115066015-tert-butyl-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 24777767(1R)-5-(1,1-Dimethylethyl)-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 (11.70 g, 44.4% ee), N-acetyl-(D)-leucine (11.78 g), and methanol (120 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-1e9b8f348a97400a811ed0f28dd11f48
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Linked notes

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