D-Psicose → HCID 69018335, compound

HRID 227190Notes

Reaction equation

HRID 227190 reaction equation
C([O:8][C:9]1[C:32]([O:33][CH3:34])=[CH:31][C:12]2[C:13](=[O:30])[N:14]3[CH2:28][C:27](=[O:29])[CH2:26][C@H:15]3[C@H:16]([OH:25])[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]=2[CH:10]=1)C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].CCOC(C)=O.CCCCCC>[C:21]([O:20][C:18]([N:17]1[C:11]2[CH:10]=[C:9]([OH:8])[C:32]([O:33][CH3:34])=[CH:31][C:12]=2[C:13](=[O:30])[N:14]2[CH2:28][C:27](=[O:29])[CH2:26][C@H:15]2[C@@H:16]1[OH:25])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 66916222HCID 66916222, compound

Product 1

HCID 69018335HCID 69018335, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A catalytic amount of 10% palladium on carbon (0.23 g) was added to a solution of cyclized compound 23 (2.3 g, 4.9 mmol) in absolute alcohol (50 mL). The reaction mixture was hydrogenated for 4 h at 30 Psi. When the reaction was complete as indicated by TLC (SiO2, 50% EtOAc-hexane) the reaction mixture was filtered through Celite, and removal of excess solvent under reduced pressure afforded the phenol 24 (4.7 g, 2.64 mmol, 53%) as a white solid: [α]25D=+115° (c=0.10, MeOH); 1H NMR (CDCl3, 400 MHz): δ 1.39 (s, 9H, Boc), 2.68-2.80 (m, 1H, 1-H), 2.87-3.02 (m, 1H, 1-H), 3.84-4.06 (m, 6H, 3-H, 11a-H, OH, 7-OMe), 4.22-4.35 (m, 1H, 3-H), 5.53-5.71 (m, 1H, 11-H), 6.02 (s, 1H, OH), 6.73 (s, 1H, 9-H), 7.20 (s, 1H, 6-H); 13C NMR (CDCl3, 100 MHz): δ 28.1, 40.4, 52.6, 56.2, 56.7, 85.9, 110.1, 115.9, 123.1, 129.9, 145.9, 148.2, 167.8, 208.1; IR (neat): 3355, 2977, 1760, 1685, 1606, 1515, 1469, 1415, 1369, 1332, 1297, 1212, 1162, 1132, 1042, 767 cm−1; MS (ES+) m/z (relative intensity) 379 (M+., 93), 380 ([M+2H]+., 25), 364 (100), 396 (75), 420 (45).

Workup

  1. filtrationwas filtered through Celite, and removal of excess solvent under reduced pressure

Sources & evidence

ORD record
ord-e26978e139fe4001abd2aff232ef0dc7
Source dataset
uspto-grants-2009_07
Patent number
US07557099B2

Reaction notes

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