N-Hydroxyphthalimide → HCID 14814229, compound

HRID 1089266Notes

Reaction equation

HRID 1089266 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:21])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:42]1[C:46](=[O:47])[C:45]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:44]2[C:43]1=[O:52].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@@H:10]([O:21][N:42]1[C:43](=[O:52])[C:44]2=[CH:51][CH:50]=[CH:49][CH:48]=[C:45]2[C:46]1=[O:47])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 14814226HCID 14814226, compound

Product 1

HCID 14814229HCID 14814229, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1,4-dibenzyloxy-2-hydroxybutane (8 g, 28 mmol) in dry tetrahydrofuran (150 ml) was added triphenylphosphine (11 g, 42 mmol) and N-hydroxyphthalimide (6.8 g, 42 mmol). The solution was treated dropwise with diethyl azodicarboxylate (6.6 ml, 42 mmol). A dark red colouration appeared, gradually fading and the solution became warm. The solution was stirred at room temperature for 16 hours, then treated with additional triphenyl phosphine (2.25 g, 8.5 mmol) N-hydroxyphthalimide (1.35 g, 8.5 mmol) and diethyl azodicarboxylate (1.35 ml, 8.5 mmol). After stirring for an additional 24 hours at room temperature, the solvent was removed under reduced pressure and the residue dissolved in ethyl acetate-hexane 1:1 (100 ml) and refrigerated. A white solid crystallised out and was filtered off. The solution was evaporated to dryness and the residue dissolved in ethyl acetate-hexane 1:1 (50 ml) and refrigerated. After filtration, the filtrate was evaporated to dryness and the residue chromatographed on silica, eluting with ethyl acetate-hexane 1:2 to give (S)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (11 g, (91%), [α]25 -17.4° (c 0.8 in ethanol); IR: υmax

Workup

  1. temperaturegradually fading and the solution became warm
  2. stirringAfter stirring for an additional 24 hours at room temperature
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in ethyl acetate-hexane 1:1 (100 ml)
  5. customA white solid crystallised out
  6. filtrationwas filtered off
  7. customThe solution was evaporated to dryness
  8. dissolutionthe residue dissolved in ethyl acetate-hexane 1:1 (50 ml)
  9. filtrationAfter filtration
  10. customthe filtrate was evaporated to dryness
  11. customthe residue chromatographed on silica
  12. washeluting with ethyl acetate-hexane 1:2

Sources & evidence

ORD record
ord-4006c8a4cf4b4923a42129cb1ced9c8b
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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