Isocyanate → [(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 1929778Notes

Reaction equation

HRID 1929778 reaction equation
[N+](C1C=CC(O[C:11](=[O:25])[NH:12][C@@H:13]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14]2)=CC=1)([O-])=O.[C:26]([NH:33][C@@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].[N-]=C=O>CO.C(Cl)Cl>[C:29]([O:28][C:26](=[O:27])[NH:33][C@@H:34]1[CH2:38][CH2:37][N:36]([C:11](=[O:25])[NH:12][C@@H:13]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14]2)[CH2:35]1)([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 68443154((R)-1-Benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester

Product 1

HCID 67022985[(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ((R)-1-benzyl-pyrrolidin-3-yl)-carbamic acid 4-nitro-phenyl ester (1 eq.) and (3R)-(+)-3-(Boc-amino)pyrrolidine in MeOH is heated using microwave radiation at 100° C. for 1 hour. The reaction mixture is reduced in vacuo. The resulting oil is dissolved in DCM and isocyanate resin (3 eq.) is added and shaken overnight. The resin was filtered off and the DCM was removed in vacuo to yield the title compound. MS (ES+) m/e 299.21 (MH+).

Workup

  1. customat 100° C.
  2. customfor 1 hour
  3. filtrationThe resin was filtered off
  4. customthe DCM was removed in vacuo

Sources & evidence

ORD record
ord-dd1f195f8cfc4bd382fdb8eb0993647c
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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