Hydrazine hydrate (1:1) → t-butyl (R)-2-(2-aminoethylamino)-3-methylbutyrate

HRID 1994296Notes

Reaction equation

HRID 1994296 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][NH:14][C@H:15]([CH:23]([CH3:25])[CH3:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O.NN>C(O)C>[NH2:3][CH2:12][CH2:13][NH:14][C@H:15]([CH:23]([CH3:25])[CH3:24])[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86619835HCID 86619835, compound

Product 1

HCID 86619836t-butyl (R)-2-(2-aminoethylamino)-3-methylbutyrateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

t-Butyl (R)-2-(2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethylamino)-3-methylbutyrate (6.60 g; 19.05 mmol) was dissolved in ethanol (100 ml). Hydrazine hydrate (4.62 ml; 95.25 mmol) was added, and the reaction mixture was heated under reflux for 2 h. The solid was filtered off with suction through kieselguhr and washed with ethanol (100 ml). The solvent was removed and the residue was partitioned between saturated NaHCO3 solution (150 ml) and CH2Cl2 (150 ml). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×; 100 ml). The combined organic phases were dried over MgSO4. Removal of the solvent under reduced pressure resulted in t-butyl (R)-2-(2-aminoethylamino)-3-methylbutyrate (4.60 g; 19.05 mmol). MS: 217.25 (M+H); Rt: 0.69 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. filtrationThe solid was filtered off with suction through kieselguhr
  4. washwashed with ethanol (100 ml)
  5. customThe solvent was removed
  6. customthe residue was partitioned between saturated NaHCO3 solution (150 ml) and CH2Cl2 (150 ml)
  7. customThe phases were separated
  8. extractionthe aqueous phase was extracted with CH2Cl2 (2×; 100 ml)
  9. dry with materialThe combined organic phases were dried over MgSO4
  10. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b973eba268064b688e5ab4e0cfb81c47
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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