Hydrazine hydrate (1:1) → Tert-butyl 3-amino-3-phenylpropylcarbamate

HRID 1809666Notes

Reaction equation

HRID 1809666 reaction equation
O.NN.[C:4]([O:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH:13]([N:20]1C(=O)C2C(=CC=CC=2)C1=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:7])([CH3:6])[CH3:5]>C1COCC1.CO>[C:4]([O:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 578268242-[3-(Boc-amino)-1-phenylpropyl]isoindoline-1,3-dione

Product 1

HCID 57826906Tert-butyl 3-amino-3-phenylpropylcarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

85% Hydrazine hydrate (5.1 mL, 74 mmol) was added to a solution of [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propyl]-carbamic acid tert-butyl ester (2.8 g, 7.4 mmol) in THF (25 mL) and MeOH (25 mL). The resulting mixture was heated at 65° C. for 6 hours. Then the precipitate was filtered, and the filtrate was concentrated under reduced pressure to give crude product which was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3H2O) to give (3-amino-3-phenyl-propyl)-carbamic acid tert-butyl ester as an off-white solid. (Yield 1.7 g, 92%).

Workup

  1. filtrationThen the precipitate was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give crude product which
  4. customwas purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3H2O)

Sources & evidence

ORD record
ord-3373c18e7c8a4972b7f9534698db76bd
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

Loading…