Methylamine → tert-butyl N-(2-amino-2-phenylethyl)carbamate

HRID 1960970Notes

Reaction equation

HRID 1960970 reaction equation
CC([N:5]([CH2:9][CH:10]([N:17]1C(=O)C2C(=CC=CC=2)C1=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](=[O:8])[O-:7])(C)C.CN.NN>CO>[NH2:17][CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:5][C:6](=[O:8])[O:7][C:11]([CH3:16])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 9321HydrazineHCID 86633536HCID 86633536, compound

Product 1

HCID 2771847tert-butyl N-(2-amino-2-phenylethyl)carbamateYield 170.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethylethyl[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-phenylethyl]carbamate (2 g, 5.46 mmol) and either MeNH2 (40 wt % in H2O, 10 eq.) or NH2NH2 (10 eq.) in MeOH (0.5M, 10 mL) was heated to 60° C. in a sealed tube. After 12 h, the solution was concentrated and purified via column chromatography (silica-dry load, 2% MeOH in DCM (1% NH4OH)) affording the title compound (1.1 g, 85%) as a white solid: LC-MS (ES) m/z=237 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. custompurified via column chromatography (silica-dry load, 2% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-91dbbf823d8444d4be6ef00f18d84308
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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