1-Azido-1-deoxy-4-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine

HRID 2372149Notes

Reaction equation

HRID 2372149 reaction equation
[N:1]([CH2:4][C@H:5]([C@@H:14]([C@H:23]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)OS(C)(=O)=O)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+]=[N-]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:7]([O:6][C@H:5]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:23]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:1][CH2:4]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 1

HCID 228428751-Azido-1-deoxy-4-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol

Product 1

HCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidineYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Azido-1-deoxy-4-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol (4.5 g, 7.98 mmol) is dissolved in a 1:1 mixture of ethanol and ethyl acetate (30 mL) and Palladium black (0.234 g) is added. The mixture is stirred under hydrogen at atmospheric pressure overnight. The catalyst is filtered off and the solvents evaporated under reduced pressure. Flash chromatography on silica gel and elution with a 95:5 mixture of ethyl acetate and methanol yield 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol (2.76 g, 86%) as an oil.

Workup

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe solvents evaporated under reduced pressure
  4. washFlash chromatography on silica gel and elution
  5. additionwith a 95:5 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-2ba28b24c9f046cca3b6e2ccd0cf3c79
Source dataset
uspto-grants-1992_03
Patent number
US05097023

Reaction notes

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