HCID 69812729, compound → HCID 68761292, compound

HRID 529080Notes

Reaction equation

HRID 529080 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:17]3([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[CH2:16][N:15]([C:30]3[C:31]4[C@H:38]([CH3:39])[CH2:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[C:12]2=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:17]3([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]3)[CH2:16][N:15]([C:30]3[C:31]4[C@H:38]([CH3:39])[CH2:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[C:12]2=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 69812729HCID 69812729, compound

Product 1

HCID 68761292HCID 68761292, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-tert-butyl 5-(benzyloxy)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.80 g, 1.5 mmol) in MeOH (20 mL) under N2 was added 10% Pd/C (0.20 g). The reaction vessel was evacuated under vacuum and hydrogenated under H2 (50 psi) for 48 hours. The hydrogen gas was evacuated and the catalyst was removed by filtration. The filtrate was concentrated. The residue was purified by flash chromatography (DCM:MeOH, 30:1) to give (R)-tert-butyl 5-hydroxy-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.40 g, 60%) as an oil. LCMS (APCI+) m/z 437 [M+H]+; Rt=3.42 min.

Workup

  1. customThe reaction vessel was evacuated under vacuum and hydrogenated under H2 (50 psi) for 48 hours
  2. customThe hydrogen gas was evacuated
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by flash chromatography (DCM:MeOH, 30:1)

Sources & evidence

ORD record
ord-61f75d8652144752be39d807bdd07314
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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