Hydrochloric Acid → HCID 68776274, compound

HRID 1471389Notes

Reaction equation

HRID 1471389 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]=[CH:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:3]1[C:12]([OH:14])=[O:13].[C:15]([O-])([O-])=O.[K+].[K+].CI.Cl>CN(C=O)C>[CH3:1][C@H:2]1[CH2:11][CH:10]=[CH:9][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8]2)[C@@H:3]1[C:12]([O:14][CH3:15])=[O:13].[CH3:1][C@H:2]1[CH2:11][CH:10]=[CH:9][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8]2)[C@H:3]1[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68722407HCID 68722407, compound

Product 2

HCID 68771814HCID 68771814, compoundYield 10%HCID 68776274HCID 68776274, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 5° C., a solution of 7-methylspiro[4.5]dec-9-ene-6-carboxylic acid (1.4 g, 7.2 mmol) in DMF was treated with K2CO3 (1.1 g, 7.9 mmol). The resulting mixture was stirred for 30 min., treated with methyl iodide (0.67 ml, 10.8 mmol), stirred at 20° C. for 2 h, poured into cold 2N aqueous HCl (20 ml), and extracted twice with hexane (70 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (170 g SiO2, pentane/diethyl ether 80:1) of the crude product (1.4 g) gave rel-(6R,7S)-methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (0.15 g, 10%) and rel-(6S,7S)-methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (0.53 g, 35%).

Workup

  1. stirringstirred at 20° C. for 2 h
  2. extractionextracted twice with hexane (70 ml)
  3. washThe combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0bbab42a07dc4bc892f9946265d20686
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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