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

HRID 521383Notes

Reaction equation

HRID 521383 reaction equation
[CH3:1][C@H:2]1[C:10]2[C:9]([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)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[CH3:1][C@H:2]1[C:10]2[C:9]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]3)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 67438528(R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67436185(R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperidine-1-carboxylateYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Pd/C (40 mg) was added to a solution of (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (63 mg, 0.20 mmol) in EtOAc (4 mL). The mixture was stirred at room temperature under a hydrogen atmosphere overnight. The mixture was filtered through celite and concentrated to give (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperidine-1-carboxylate as an oil (58 mg, 91%), which was used further without purification.

Workup

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

Sources & evidence

ORD record
ord-0fab99cd14c244ff9f9fc1d4a7dba007
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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