tert-Butyl carbazate → N1-(tert-butoxycarbonyl)-N2-(4-biphenylylmethyl)hydrazine

HRID 1043979Notes

Reaction equation

HRID 1043979 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[NH:25][NH2:26]>CN(C=O)C>[C:29]([O:28][C:24]([NH:25][NH:26][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 10637828N1-(tert-butoxycarbonyl)-N2-(4-biphenylylmethyl)hydrazineYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Bromomethyl)biphenyl (2.0 g, 8.1 mmol, 1.0 eq.) and DIPEA (1.4 mL, 1.0 eq.) were dissolved in DMF (40.0 mL). t-Butyl carbazate (2.1 g, 16.2 mmol, 2.0 eq.) was added and the mixture was stirred at room temperature overnight. The mixture was partially concentrated, and the residue was partitioned between EtOAc and a saturated aqueous NaHCO3 solution. The EtOAc layer was then dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc/hexanes with 0.5% DIPEA) to yield compound 1, N′-biphenyl-4-ylmethyl-hydrazinecarboxylic acid t-butyl ester (1.7 g).

Workup

  1. concentrationThe mixture was partially concentrated
  2. customthe residue was partitioned between EtOAc
  3. dry with materialThe EtOAc layer was then dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0-60% EtOAc/hexanes with 0.5% DIPEA)

Sources & evidence

ORD record
ord-c5a870ffd848454c9efcb41a44c92624
Source dataset
uspto-grants-2013_10
Patent number
US08563512B2

Reaction notes

Loading…