Hydrazine hydrate (1:1) → [(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

HRID 1711201Notes

Reaction equation

HRID 1711201 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:9][NH2:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68775880[(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-phenylethyl]-carbamic acid tert-butyl ester

Product 1

HCID 15675183[(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the crude phthalimide and hydrazine hydrate (10.0 ml, 177 mmol) in EtOH (200 ml) was stirred at reflux for 1 hour. Once cooled, the mixture was concentrated under reduced pressure. The residue was suspended in 1.5M HCl (200 ml) and washed with CH2Cl2 (50 ml×3). The organic solution was extracted with 4M HCl (50 ml×2). The combined aqueous extracts were made basic with 10M NaOH (100 ml) and extracted with CH2Cl2 (50 ml×4). This organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification gave ((R)-2-amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester as an off-white solid (2.41 g, 51% over 2 steps).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureOnce cooled
  3. concentrationthe mixture was concentrated under reduced pressure
  4. washwashed with CH2Cl2 (50 ml×3)
  5. extractionThe organic solution was extracted with 4M HCl (50 ml×2)
  6. extractionextracted with CH2Cl2 (50 ml×4)
  7. dry with materialThis organic solution was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification

Sources & evidence

ORD record
ord-e6d40abd8fda438eaae30f798e2a01ec
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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