Potassium Carbonate → (S)-1-((3AR,5S,6AR)-2,2-Dimethyltetrahydrofuro[2,3-D][1,3]dioxol-5-YL)propan-1-OL

HRID 60699Notes

Reaction equation

HRID 60699 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]([C@H:14]2[O:23][C@@H:17]3[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]3[CH2:15]2)[CH2:12][CH3:13])=O)=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:22][C:19]1([CH3:21])[O:18][C@H:17]2[O:23][C@H:14]([C@@H:11]([OH:10])[CH2:12][CH3:13])[CH2:15][C@H:16]2[O:20]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 121396359HCID 121396359, compound2×

Product 1

HCID 121396307(S)-1-((3AR,5S,6AR)-2,2-Dimethyltetrahydrofuro[2,3-D][1,3]dioxol-5-YL)propan-1-OLYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl] 4-nitrobenzoate (compound 6d, 100 g, 285 mmol) in methanol (1200 mL) was added K2CO3 (78.7 g, 570 mmol). After being stirred at room temperature for 10 minutes, the resulted mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:8 EtOAc in petroleum ether) to afford 54.7 g of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 6e) as a slight yellow solid.

Workup

  1. filtrationthe resulted mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:8 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-757f90cc96524779925eb0c1e9fed0d6
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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