Pyridine → HCID 53798011, compound

HRID 416123Notes

Reaction equation

HRID 416123 reaction equation
[O:1]1[CH2:5][C@H:4]([OH:6])[C@@H:3]2[O:7][CH2:8][C@@H:9]([OH:10])[C@@H:2]12.[C:11]1(C)[C:12]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.N1C=CC=C[CH:23]=1>>[OH:6][C@H:4]1[C@H:3]2[O:7][CH2:8][C@H:9]([O:10][S:17]([C:12]3[CH:11]=[CH:16][C:15]([CH3:23])=[CH:14][CH:13]=3)(=[O:18])=[O:19])[C@H:2]2[O:1][CH2:5]1.[OH:6][C@@H:4]1[C@H:3]2[O:7][CH2:8][C@@H:9]([O:10][S:17]([C:12]3[CH:11]=[CH:16][C:15]([CH3:23])=[CH:14][CH:13]=3)(=[O:18])=[O:19])[C@H:2]2[O:1][CH2:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 12304541HCID 12304541, compound

Product 2

HCID 53798011HCID 53798011, compoundHCID 57983756HCID 57983756, compound

Procedure

A solution of 8.76 g of (3S,3aS,6R,6aR)-hexahydro-furo[3,2-b]furan-3,6-diol in 80 ml of pyridine is stirred for 16 hours with 13.7 g of toluenesulfonylchloride, solvent is distilled off and the distillation residue is dissolved in EtAc and extracted with 1N HCl, saturated aqueous NaHCO3-solution and H2O. The organic layer obtained is dried, solvent is evaporated and the evaporation residue is subjected to chromatography. Toluene-4-sulfonic acid (3S,3aS,6R,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (a) and toluene-4-sulfonic acid (3R,3aS,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (b) are obtained. 1H-NMR(DMSO-d6) of form (a): 7.8 (d,2H,Ar—H,J=8.2 Hz), 7.5 (d,2H,Ar—H,J=8.6 Hz), 4.95 (d,1H,6-OH), 4.8 (m, 1H, H-3), 4.42 (dd,1H,H-6a,J=4.6 and 4.8 Hz), 4.38 (d,1H,H-3a,J=4.6), 4.08 (m,1H,H-6), 3.8 (m,2H,2×H-2), 3.7, 3.25 (2×dd, 2H, 2×H-5), 2.4 (s, 3H, Ar—CH3).

Workup

  1. distillationis distilled off
  2. dissolutionthe distillation residue is dissolved in EtAc
  3. extractionextracted with 1N HCl, saturated aqueous NaHCO3-solution and H2O
  4. customThe organic layer obtained
  5. customis dried
  6. customsolvent is evaporated

Sources & evidence

ORD record
ord-456a7623e25648f0a68a7b8eddeee2f4
Source dataset
uspto-grants-2012_01
Patent number
US08088823B2

Reaction notes

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