4-Nitrophenyl chloroformate → ((R)-1-Benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester

HRID 1929777Notes

Reaction equation

HRID 1929777 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].N1C=CC=CC=1.C(Cl)Cl.[CH2:23]([N:30]1[CH2:34][CH2:33][C@@H:32]([NH2:35])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2](=[O:3])[NH:35][C@@H:32]2[CH2:33][CH2:34][N:30]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:31]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 21875418Pyridine methylene chloride

Product 1

HCID 68443154((R)-1-Benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitro-phenyl chloroformate (1 eq.) is added dropwise to a solution of pyridine/DCM (1:5) at 0° C. The reaction mixture is kept at 0° C. and a solution of (R)-1-benzyl-pyrrolidin-3-ylamine (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at room temperature overnight. The reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM. The organics are washed with water, saturated sodium hydrogen carbonate solution and brine. The combined organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound. MS (ES+) m/e 342.10 (MH+).

Workup

  1. customis kept at 0° C.
  2. customThe reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM
  3. washThe organics are washed with water, saturated sodium hydrogen carbonate solution and brine
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2c9cbd79dc574e44b8da3a44c811b2d0
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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