(3R)-1-benzylpyrrolidin-3-amine → {4-[3-((R)-1-Benzyl-pyrrolidin-3-yl)-ureido]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1929775Notes

Reaction equation

HRID 1929775 reaction equation
C1(O[C:8](=[O:24])[NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)C=CC=CC=1.[CH2:25]([N:32]1[CH2:36][CH2:35][C@@H:34]([NH2:37])[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[C:20]([O:19][C:17](=[O:18])[NH:16][CH:13]1[CH2:12][CH2:11][CH:10]([NH:9][C:8]([NH:37][C@@H:34]2[CH2:35][CH2:36][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:33]2)=[O:24])[CH2:15][CH2:14]1)([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 67022954(4-tert-Butoxycarbonylamino-cyclohexyl)-carbamic acid phenyl ester

Product 1

HCID 67022947{4-[3-((R)-1-Benzyl-pyrrolidin-3-yl)-ureido]-cyclohexyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid phenyl ester (1 eq.) and (R)-1-benzyl-pyrrolidin-3-ylamine (1 eq.) in MeOH is heated using microwave radiation at 100° C. for 30 minutes. The resulting solution is purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water 0.1% HCl) to afford the title compound.

Workup

  1. customat 100° C.
  2. customfor 30 minutes
  3. customThe resulting solution is purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water 0.1% HCl)

Sources & evidence

ORD record
ord-ccb6cc2182e64a3980724d68bcba1c83
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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