Triethylamine → 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

HRID 1959450Notes

Reaction equation

HRID 1959450 reaction equation
Br[C:2]1[N:3]=[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[CH2:34]1[C@@H:38]2[CH2:39][CH2:40][CH:41]([OH:42])[C@@H:37]2[CH2:36][NH:35]1.C(N(CC)CC)C>CN(C=O)C>[OH:42][CH:41]1[C@@H:37]2[CH2:36][N:35]([C:2]3[N:3]=[C:4]([C:23]4[O:24][C:25]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[N:26][N:27]=4)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[N:6][CH:7]=3)[CH2:34][C@@H:38]2[CH2:39][CH2:40]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55299595(3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-olHCID 59471994Tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

Product 1

HCID 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-carbamateYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (115 mg, 0.22 mmol), (3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol (73 mg, 0.57 mmol) and triethyl amine (34 mg, 46 μL, 0.33 mmol) in DMF was heated to 90° C. for 90 minutes. The solvent was removed 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-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, 83%). LC/MS m/z 465.5 [M+H-Boc]+.

Workup

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

Sources & evidence

ORD record
ord-efa11a57192b4cc1a33c6b94ef4a55c9
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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