HCID 86633042, compound → HCID 58208601, compound

HRID 333027Notes

Reaction equation

HRID 333027 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OC(C)(C)C)=O)[CH2:8][C@H:9]([O:10][S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C@H:5]2[O:4][CH2:3]1.[H][H]>[Pd].C(O)C>[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([O:10][C@H:9]2[CH2:8][NH:7][C@@H:6]3[C@@H:2]([OH:1])[CH2:3][O:4][C@H:5]23)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 86633042HCID 86633042, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58208601HCID 58208601, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation (3R, 3aR, 6S, 6aS)-tert-Butyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b]pyrrole-4(5H)carboxylate (35). Ethanol (20 mL) was added dropwise to a mixture of 10% palladium on charcoal (50 mg) and anti-(33) (578 mg, 1.33 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 1.5 hours before filtering the mixture through celite in vacuo. The filter cake was washed with ethanol then the solvents removed in vacuo from the filtrate to obtain (3R, 3aR, 6S, 6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate which was used without further purification.

Workup

  1. filtrationbefore filtering the mixture through celite in vacuo
  2. washThe filter cake was washed with ethanol
  3. customthe solvents removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-07d6bd31b1b24b5fa16ba43088647a02
Source dataset
uspto-grants-2014_11
Patent number
US08877927B2

Reaction notes

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