Phthalimide → HCID 68229195, compound

HRID 1853900Notes

Reaction equation

HRID 1853900 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:11])[CH2:9]O)=[C:4]([F:12])[CH:3]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:11])[CH2:9][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86689561HCID 86689561, compound

Product 1

HCID 68229195HCID 68229195, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(4-bromo-2-fluorophenyl)propan-1-ol (800 mg, 3.43 mmol), phthalimide (554 mg, 3.77 mmol), and triphenylphosphine (1.34 g, 5.14 mmol) in THF (2 mL) was added DIAD (1 mL, 5.14 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h and evaporated under vacuum. Flash chromatography of the residue afforded the desired product (1 g, 81%) as a white solid ESI MS m/z 363 [C17H13BrFNO2+H]+

Workup

  1. customevaporated under vacuum

Sources & evidence

ORD record
ord-711624c99196496eb2ba8ea06790d4b9
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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