{(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester → N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-yl}-propionamide

HRID 1696976Notes

Reaction equation

HRID 1696976 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@H:25]3[C@H:32]4[C@H:28]([O:29][C:30]([CH3:34])([CH3:33])[O:31]4)[C@@H:27]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH2:26]3)=[C:18]([NH:40][CH2:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:17]=2)[CH2:12]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@H:25]3[C@@H:32]4[O:31][C:30]([CH3:34])([CH3:33])[O:29][C@@H:28]4[C@@H:27]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH2:26]3)=[C:18]([NH:40][CH2:41][CH:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:17]=2)[CH2:12]1

Participants

4

Reactant 1

HCID 66630309{(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester

Product 1

HCID 66629700N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-yl}-propionamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of {(R)-1-[9-((3aS,4R,6S,6aR)-2,2-dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl- ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester (0.598 g, 0.79 mmol) in ethanol (7.5 ml) under an inert atmosphere of Argon is added palladium hydroxide on carbon (10 mg). The reaction mixture is purged with Argon and placed under an atmosphere of hydrogen overnight. The mixture is filtered and purified by chromatography on silica eluting with 5% MeOH in DCM to yield the title d compound. [MH+ 611].

Workup

  1. customThe reaction mixture is purged with Argon
  2. filtrationThe mixture is filtered
  3. custompurified by chromatography on silica eluting with 5% MeOH in DCM
  4. customto yield the title d compound

Sources & evidence

ORD record
ord-1409ba4ca8e14064bb30135ed2a28ab9
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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