Triacetoxyperiodinane → tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

HRID 1959451Notes

Reaction equation

HRID 1959451 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH2:7][N:8]([C:10]3[N:11]=[C:12]([C:31]4[O:32][C:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[N:34][N:35]=4)[C:13]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14][CH:15]=3)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[C@@H:6]2[CH2:7][N:8]([C:10]3[N:11]=[C:12]([C:31]4[O:32][C:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[N:34][N:35]=4)[C:13]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[N:14][CH:15]=3)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66745529tert-butyl N-[5-[(3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

Product 1

HCID 66744152tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamateYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl N-[5-[(3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (104 mg, 0.18 mmol) in DCM (1 mL) at 0° C. was treated with a solution of Dess-Martin periodinane (921 μL 0.3 M, 0.28 mmol) in DCM. The reaction mixture was warmed to room temperature and stirred overnight. The solvent was evaporated under reduced pressure and the crude material was purified by silica gel column chromatography using 5-60% EtOAc in DCM to yield tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (57 mg, 55%) as a yellow solid. LC/MS m/z 463.5 [M+H-Boc]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-78097a36d81440db9b9f4f58db2bd0f9
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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