Sodium hydride → HCID 6932371, compound

HRID 1408922Notes

Reaction equation

HRID 1408922 reaction equation
[H-].[Na+].[CH3:3][C@@:4]1([C:15]([O:17][CH3:18])=[O:16])[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]1([CH3:14])[CH3:13]>O1CCCC1>[CH3:3][C@@:4]1([C:15]([O:17][CH3:18])=[O:16])[CH2:8][CH2:7][C@@H:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]1([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 2770979HCID 2770979, compound

Product 1

HCID 6932371HCID 6932371, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.788 g, 19.71 mmol, 60% suspension in mineral oil) was added to a solution of (1R,3S)-dimethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate (1.50 g, 6.57 mmol, from Step 1) in tetrahydrofuran (20 mL) at room temperature. The resulting mixture was heated to reflux for 1 h, cooled to room temperature, and carefully quenched with saturated ammonium chloride (10 mL). After dilution with ethyl acetate (100 mL), the mixture was washed with water, brine, dried (MgSO4), filtered and concentrated to give crude product (1.45 g), which was found to be roughly a 1:1 mixture of the desired (1R,3R)-product and the (1R,3S)-starting material based on 1H NMR analysis. The mixture was taken to the next reaction without purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customcarefully quenched with saturated ammonium chloride (10 mL)
  4. washAfter dilution with ethyl acetate (100 mL), the mixture was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6adc6f35823f4fcc8626c9ac23cd51d9
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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