N-Hydroxyphthalimide → HCID 14814230, compound

HRID 1089263Notes

Reaction equation

HRID 1089263 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]>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

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 14814227HCID 14814227, compound

Product 1

HCID 14814230HCID 14814230, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1,4-dibenzyloxy-2-hydroxybutane (5 g, 17.5 mmol) in dry tetrahydrofuran (100 ml) was added triphenylphosphine (5.1 g, 19.2 mmol) and N-hydroxyphthalimide (3.1 g, 19.2 mmol). The solution was treated dropwise with diethyl azadicarboxylate (3 ml, 19.2 mmol). A red colouration appeared, gradually fading and the solution became warm. The solution was stirred at room temperature for 48 hours and the solvent removed under vacuum. The residue was dissolved in ethylacetatehexane 1:1 (100 ml) and refrigerated. A white solid crystallised out and was filtered off. The solution was evaporated to dryness and the residue chromatographed on silica, eluting with ethylacetate-hexane 1:2 to give (R)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (4.6 g, 61%), [α]D25 +16.4° (c 1.3 in ethanol); IR: υmax (film) 3090, 3060, 3030, 2930, 2860, 1810, 1790, 1730, 1610, 1495, 1465, 1450, 1370, 1240, 1190, 1120, 1100, 1080, 1030, 1015, 980, 880, 785, 740, 700 cm-1 ; 1H NMR: δH (CDCl3) 2.1 (2H, m, CH2), 3.75 (4 H, m, 2×CH2), 4.5 (5H, m, 2×CH2 plus CH), 7.1-7.9 (14 H, m, 2×C6H5 plus C6H4); m/z (FAB) MH+ 432.

Workup

  1. additionThe solution was treated dropwise with diethyl azadicarboxylate (3 ml, 19.2 mmol)
  2. temperaturegradually fading and the solution became warm
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue was dissolved in ethylacetatehexane 1:1 (100 ml)
  5. customA white solid crystallised out
  6. filtrationwas filtered off
  7. customThe solution was evaporated to dryness
  8. customthe residue chromatographed on silica
  9. washeluting with ethylacetate-hexane 1:2

Sources & evidence

ORD record
ord-cd5ad04297b44e4291ddf57826e2ee22
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

Loading…