N-Hydroxyphthalimide → 2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

HRID 78997Notes

Reaction equation

HRID 78997 reaction equation
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].O[N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].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>[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][O:9][N:14]1[C:18](=[O:19])[C:17]2[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]1=[O:24])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15688069(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

Product 1

HCID 583743222-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (53.0 g, 0.28 mol), N-hydroxyphthalimide (47.0 g, 0.29 mol) and triphenylphosphine (77.9 g, 0.30 mol) in THF (200 ml) at 0° C. was added dropwise DIAD (56.8 ml, 0.29 mol). During the addition the reagents dissolved and the solution turned a dark red colour before fading to pale yellow colour on completion of the addition. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the resultant residue re-dissolved in diethyl ether. The suspension was filtered and the filtrate was concentrated in vacuo to yield the crude title compound as a pale yellow oil. The material was used without further purification in the subsequent step.

Workup

  1. additionDuring the addition the reagents
  2. dissolutiondissolved
  3. additionbefore fading to pale yellow colour on completion of the addition
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe resultant residue re-dissolved in diethyl ether
  6. filtrationThe suspension was filtered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b60a2cb54444419c912959b2aecaceca
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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