dibenzyl ((2S,3R,4R,5S)-3,4-dihydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate → (2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

HRID 1647332Notes

Reaction equation

HRID 1647332 reaction equation
C(OC([NH:11][C@H:12]([C@@H:20]([OH:42])[C@H:21]([OH:41])[C@@H:22]([NH:30]C(OCC1C=CC=CC=1)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[H][H]>C1COCC1.C(O)C.[Pd]>[NH2:11][C@H:12]([C@@H:20]([OH:42])[C@H:21]([OH:41])[C@@H:22]([NH2:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 10393187dibenzyl ((2S,3R,4R,5S)-3,4-dihydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 10990240(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexaneYield 109.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.432 g (18.36 mmol) of compound 6 in 500 ml THF and 500 ml ethyl alcohol was stirred with 1.043 g of 10% palladium on carbon at room 15 temperature. for 18 h over 1 atmosphere hydrogen pressure. The mixture was filtered through celite pad and the filtrate was concentrated to provide 6.06 g (yield) of compound 7. The oil was triturated with diethyl ether and the white solid was filtered and washed to provide pure 7 (M. P. 92-94).

Workup

  1. filtrationThe mixture was filtered through celite pad
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-58932c7b665f4dcab6583c556cdf6ba6
Source dataset
uspto-grants-1995_07
Patent number
US05430155

Reaction notes

Loading…