(3R)-1-benzylpyrrolidin-3-amine → HCID 51707017, compound

HRID 2382375Notes

Reaction equation

HRID 2382375 reaction equation
C1(O[C:8](=[O:16])[NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)C=CC=CC=1.[CH2:17]([N:24]1[CH2:28][CH2:27][C@@H:26]([NH2:29])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([N:24]1[CH2:28][CH2:27][C@@H:26]([NH:29][C:8]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:16])[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 6935890Phenyl pyridin-3-ylcarbamate

Product 1

HCID 51707017HCID 51707017, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pyridin-3-yl-carbamic acid phenyl ester (1.6 g) in dry THF (20 ml) is treated with (R)-1-benzyl-pyrrolidin-3-ylamine (1.9 g, 1.05 eq) and then heated using microwave radiation at 110° C. for 1000 s. The solvent is removed in vacuo and purification of the crude product by chromatography on silica eluting with DCM followed by EtOAc and EtOH affords the title compound as an oil. (MH+ 297).

Workup

  1. temperatureheated
  2. customat 110° C.
  3. customfor 1000 s
  4. customThe solvent is removed in vacuo and purification of the crude product by chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-e8c2f38bd2ea4036aa9e4ce92e7d257e
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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