HCID 59343398, compound → HCID 57792801, compound

HRID 1716457Notes

Reaction equation

HRID 1716457 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OCC3C=CC=CC=3)=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 59343398HCID 59343398, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57792801HCID 57792801, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation of (3R,3aR,6R,6aS)— Benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (34b). Ethanol (1.5 mL) was added dropwise to a mixture of 10% palladium on charcoal (10 mg) and anti-(33b) (12.0 mg, 0.028 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 1.75 hours before filtering the mixture through celite in vacuo. The filter cake was washed with ethanol (7.5 mL) then the solvents removed in vacuo from the filtrate. The residue was azeotroped with toluene (2 mL) to obtain (3R,3aR,6R,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate (7.6 mg, 89%) as a pale yellow oil which was used without further purification. TLC (Rf=0.01, EtOAc:heptane 1:1), HPLC-MS 300.1 [M+H]+, 621.2 [2M+Na]+.

Workup

  1. filtrationbefore filtering the mixture through celite in vacuo
  2. washThe filter cake was washed with ethanol (7.5 mL)
  3. customthe solvents removed in vacuo from the filtrate
  4. customThe residue was azeotroped with toluene (2 mL)

Sources & evidence

ORD record
ord-fa71e8592fff422d8f0896536b0acd81
Source dataset
uspto-grants-2010_09
Patent number
US07803803B2

Reaction notes

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