Phthalimide → HCID 59904461, compound

HRID 870747Notes

Reaction equation

HRID 870747 reaction equation
O[CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[O:8]=[C:6]1[NH:7][C@H:3]([CH2:2][N:13]2[C:9](=[O:19])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:14])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 59904461HCID 59904461, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To (S)-5-(hydroxymethyl)pyrrolidin-2-one (2.00 g, 17.39 mmol) dissolve in 25 mL THF was added phthalimide (2.81 g, 19.13 mmol), triphenylphosphine (5.01 g, 19.13 mmol) and diisopropylazodi-carboxylate (3.33 g, 19.13 mmol). This mixture was stirred for about 16 hr, and then diluted with 200 mL of hexanes and 2 mL of DCM, and then cool at −30° C. The product precipitated and was filtered and dried (4.11 g, 96%, white solid).

Workup

  1. customThe product precipitated
  2. filtrationwas filtered
  3. customdried (4.11 g, 96%, white solid)

Sources & evidence

ORD record
ord-950971f70df44036908f02d14431b8c6
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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