Potassium Carbonate → HCID 121396399, compound

HRID 60711Notes

Reaction equation

HRID 60711 reaction equation
CC1C=CC(S([O:11][CH2:12][C@H:13]([C@H:15]2[O:24][C@@H:18]3[O:19][C:20]([CH3:23])([CH3:22])[O:21][C@@H:17]3[CH2:16]2)[OH:14])(=O)=O)=CC=1.[C:25]([O-])([O-])=O.[K+].[K+]>CO>[CH3:22][C:20]1([CH3:23])[O:19][C@H:18]2[O:24][C@H:15]([C@@H:13]([OH:14])[CH2:12][O:11][CH3:25])[CH2:16][C@H:17]2[O:21]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15473566[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate2×

Product 1

HCID 121396399HCID 121396399, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [(2S)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate (compound 6a, 3.2 g, 8.9 mmol) in methanol (50 mL) was added K2CO3 (5.4 g, 40 mmol). After being stirred at room temperature for 2 hours, the resulting solution was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether) to afford 1.62 g of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanol (compound 21b) as a colorless oil.

Workup

  1. concentrationthe resulting solution was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-7c97b3248e074e44ae69ed395a51c15e
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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