N-Hydroxyphthalimide → HCID 59774397, compound

HRID 549443Notes

Reaction equation

HRID 549443 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][CH2:20][CH2:21][CH2:22][OH:23])([CH3:18])([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:44]1[C:48](=[O:49])[C:47]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:46]2[C:45]1=[O:54]>C1COCC1>[C:15]([O:19][CH2:20][CH2:21][CH2:22][O:23][N:44]1[C:48](=[O:49])[C:47]2[C:46](=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:45]1=[O:54])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 50567393-tert-Butyloxy-1-propanol

Product 1

HCID 59774397HCID 59774397, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (13.4 mL, 68 mmol) was added dropwise at 0° C. to a stirred suspension of 3-tert-butoxy-propan-1-ol (9.0 g, 68 mmol), triphenylphosphine (17.8 g, 68 mmol), and N-hydroxyphthalimide (11.1 g, 68 mmol) in THF (150 mL), and the reaction stirred for 16 h at room temperature. The solution was concentrated in vacuo and purified by silica gel chromatography (20% Et2O/hexanes) to give 15.5 g (82%) of the title compound as a faintly yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.72-7.84 (m, 4H), 4.30 (t, 2H, J=4.8 Hz), 3.58 (t, 2H, J=4.8 Hz), 1.94-2.00 (m, 2H), 1.20 (s, 9H). MS (ES) [m+H] calc'd for C15H19NO4, 278; found 278.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (20% Et2O/hexanes)

Sources & evidence

ORD record
ord-fe55118bb1314bf1952c8e9f1a9a90f3
Source dataset
uspto-grants-2011_05
Patent number
US07943659B2

Reaction notes

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