Phthalic Anhydride → (2S)-2-Phthalimido-3-phenyl-propanol

HRID 2109692

Reaction equation

HRID 2109692 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])O1.[NH2:12][C@@H:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][OH:15]>O1CCOCC1>[OH:15][CH2:14][C@@H:13]([N:12]1[C:3](=[O:10])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:11])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 447213phenylalaninol, (S)-

Product 1

HCID 11323487(2S)-2-Phthalimido-3-phenyl-propanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Isobenzofuran-1,3-dione (4.40 g, 29.76 mmol) and (S)-2-amino-3-phenylpropan-1-ol (4.50 g, 29.76 mmol) were charged into a 20 mL microwave tube along with 10 mL dioxane. The microwave tube was heated at 150° C. for 33 minutes in a Smith Synthesizer. After the reaction was complete, dioxane was evaporated off and the residue was passed through a short pad of silica gel with DCM. The resulting product (7.50 g, 89%) was used in the following step. LCMS (API-ES) m/z (%): 282.2 (100%, M++H).

Workup

  1. customdioxane was evaporated off

Sources & evidence

ORD record
ord-026f06bd477247129bb01aaf38c0fc2f
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Linked notes

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