HCID 66845407, compound → HCID 66845336, compound

HRID 1916408Notes

Reaction equation

HRID 1916408 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([O:8][CH:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([N:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)[C:12]=3[C@H:11]([CH3:31])[CH2:10]2)=[O:7])=[CH:4][CH:3]=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([O:8][C@H:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([N:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:22][CH2:23]4)[C:12]=3[C@H:11]([CH3:31])[CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66845407HCID 66845407, compound

Product 1

HCID 66845336HCID 66845336, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-tert-Butyl 4-(7-(4-bromobenzoyloxy)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (0.832 g, 1.608 mmol) was subjected to chromatography on SiO2 eluting with 2:1 hexanes:ethyl acetate to give tert-butyl 4-((5R,7R)-7-(4-bromobenzoyloxy)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (0.31 g, 37%); then switching to 1:1 hexane:ethyl acetate to give tert-butyl 4-((5R,7S)-7-(4-bromobenzoyloxy)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (415.3 mg, 49%).

Sources & evidence

ORD record
ord-427d193853b44ae695b9130458e8aa31
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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