Phthalimide → HCID 69810857, compound

HRID 529083Notes

Reaction equation

HRID 529083 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:11][N:10]([C:25]3[C:26]4[C@H:33]([CH3:34])[CH2:32][CH2:31][C:27]=4[N:28]=[CH:29][N:30]=3)[C:7]2=[CH:8][CH:9]=1.[C:35]1(=[O:45])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](=[O:44])[NH:36]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:45]=[C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](=[O:44])[N:36]1[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]3)[CH2:11][N:10]([C:25]3[C:26]4[C@H:33]([CH3:34])[CH2:32][CH2:31][C:27]=4[N:28]=[CH:29][N:30]=3)[C:7]2=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69810729HCID 69810729, compound

Product 1

HCID 69810857HCID 69810857, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-tert-butyl 5-(2-hydroxyethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.021 g, 0.045 mmol) in THF (0.2 mL) was added isoindoline-1,3-dione (0.020 g, 0.14 mmol) and PS—PPh3 (0.081 g, 0.14 mmol). The solution was cooled to 0° C. and DEAD (0.021 ml, 0.14 mmol) was added dropwise. The reaction was allowed to stir with warming to about room temperature for 2 hours. The reaction was filtered and the solvent was evaporated. The crude residue was purified by column chromatography (1-3% MeOH/DCM) to yield (R)-tert-butyl 5-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.014 g, 52%). LCMS (APCI+) m/z 594 [M+H]+; Rt=4.15 min.

Workup

  1. temperaturewith warming to about room temperature for 2 hours
  2. filtrationThe reaction was filtered
  3. customthe solvent was evaporated
  4. customThe crude residue was purified by column chromatography (1-3% MeOH/DCM)

Sources & evidence

ORD record
ord-6a7a89d18cb34df4aa27ae0566f1c9ef
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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