Hydrazine hydrate (1:1) → HCID 28799790, compound

HRID 2279487Notes

Reaction equation

HRID 2279487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C1COCC1.CO.O.NN>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH2:12])[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21899815MeOH tetrahydrofuranHCID 86705491HCID 86705491, compound

Product 1

HCID 28799790HCID 28799790, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 160 (2.05 g, 5.21 mmol) and THF:MeOH (1:1, 40 mL) at RT was added hydrazine monohydrate (1.31 mL, 26.1 mmol) and the reaction was heated to 50° C. and stirred for 24 h. THF (20 mL) was added and precipitated phthalimide was filtered and discarded. The filtrate was washed with brine, extracted with DCM and the organic phases combined, dried (Na2SO4), filtered and concentrated to afford 1.18 g (89%) of (R)-1-(3,4-dichloro phenyl)propan-1-amine (162) as a viscous yellow oil. The 19F NMR of the Mosher amide indicated an ee of 93% based on peaks at −69.28 and −69.31.

Workup

  1. customprecipitated phthalimide
  2. filtrationwas filtered
  3. washThe filtrate was washed with brine
  4. extractionextracted with DCM
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e9a6f76e62547a8a3cb6b5df0e0fcca
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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