HCID 69812729, compound → HCID 68761292, compound

HRID 2190020Notes

Reaction equation

HRID 2190020 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-be1316d55fed434c8f9f2e714749aef3
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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