Benzyl chloroformate → HCID 67295242, compound

HRID 589198Notes

Reaction equation

HRID 589198 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:22](Cl)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 672944095-Bromo-2-(2-pyrrolidinyl)pyridine

Product 1

HCID 67295242HCID 67295242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-bromo-2-(pyrrolidin-2-yl)pyridine (2.67 g, 11.8 mmol) in DCM (20 mL) at 0° C. was added DIEA (1.5 eq), followed by CbzCl (1.1 eq). The resulting clear solution was warmed to it and stirred for 2 h. The reaction mixture was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.35 in 50% EtOAc) to afford the titled compound as a brownish oil (3.63 g).

Workup

  1. temperatureThe resulting clear solution was warmed to it
  2. washThe reaction mixture was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.35 in 50% EtOAc)

Sources & evidence

ORD record
ord-9cd9138fe20842db8f597b5b7a95affe
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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