Hydrazine → 1,1-Dimethylethyl [2-amino-2-(1-naphthalenyl)ethyl]carbamate

HRID 1967097Notes

Reaction equation

HRID 1967097 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].NN>CO>[NH2:3][CH:12]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 578264601,1-dimethylethyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(1-naphthalenyl)ethyl]carbamate

Product 1

HCID 578264871,1-Dimethylethyl [2-amino-2-(1-naphthalenyl)ethyl]carbamateYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(1-naphthalenyl)ethyl]carbamate (1.29 g, 3.1 mmol) in MeOH (30 mL) was added anhydrous hydrazine (0.5 mL, 15.5 mmol) at 25° C. After 12 h, the solution was partitioned between DCM/H2O. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly yielding the title compound as a white solid (491 mg, 1.72 mmole, 55%): LCMS (ES) m/z 287 (M+H)+.

Workup

  1. customthe solution was partitioned between DCM/H2O
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8594798075d14179bb71bd9e3d8fe56d
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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