tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperidine-1-carboxylate

HRID 521380Notes

Reaction equation

HRID 521380 reaction equation
[OH:1][C@H:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[C:5]=2[C@H:4]([CH3:24])[CH2:3]1>CCOC(C)=O.[Pd]>[OH:1][C@H:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]3)[C:5]=2[C@H:4]([CH3:24])[CH2:3]1

Participants

4

Reactant 1

HCID 67438475tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67438470tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Pd/C (10 mg) was added to a solution of tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (17 mg, 0.05 mmol) in EtOAc (1 mL). The mixture was stirred at room temperature under a hydrogen atmosphere overnight. The mixture was filtered through celite and concentrated to give tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperidine-1-carboxylate as an oil (13 mg, 78%), which was used further without purification.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-70872f9c2bef4ca891b0b425f1852667
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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