Phthalimide → HCID 131734608, compound

HRID 595974Notes

Reaction equation

HRID 595974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8](O)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 131734607HCID 131734607, compound

Product 1

HCID 131734608HCID 131734608, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (R)-tert-butyl (2-(3-chlorophenyl)-2-hydroxyethyl)(methyl)carbamate (2.0 g, 7.00 mmol) in THF (23.33 mL) was added phthalimide (1.339 g, 9.10 mmol) and PPh3 (3 mmol of PPh3/1 g of resin, 2.34 g, 7.02 mmol). Then DTBAD (1.660 g, 7.21 mmol) in THF was slowly added at room temperature, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through Celite® and washed with EtOAc. The filtrate was concentrated, redissolved in EtOAc, washed with sat. Na2CO3, water and brine, dried over sodium sulfate, filtered off, and concentrated. The crude product was purified by flash chromatography to afford (S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)(methyl)carbamate (1.96 g, 4.72 mmol, 67.5%). LCMS (m/z): 315.1 (MH+-100), 1.19 min.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionredissolved in EtOAc
  5. washwashed with sat. Na2CO3, water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered off
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-54cea56079c74ded81d6000d75f0c0ca
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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