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

HRID 2272632Notes

Reaction equation

HRID 2272632 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-000e2c8fdc6f41f0864f8adbe0f35c89
Source dataset
uspto-grants-2015_09
Patent number
US09120758B2

Reaction notes

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