Hydrochloric Acid → HCID 57771477, compound

HRID 2070540Notes

Reaction equation

HRID 2070540 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:10](OS(C)(=O)=O)[CH2:9][CH2:8][C:7]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:6]1)=[O:4].N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH2:6][C:7]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:8][CH2:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86632263HCID 86632263, compound

Product 1

HCID 57771477HCID 57771477, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of trans-3-methanesulfonyloxy-spiro[5.5]undecane-2-carboxylic acid methyl ester (3.0 g) obtained in Step 5 in tetrahydrofuran (20 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.65 mL), followed by stirring the reaction mixture at 70° C. for 6 hours. After cooling down to room temperature and adding 2N aqueous hydrochloric acid solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated to give spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester (1.9 g).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f12e16a65a2846b98eeacf55f0f7d2b7
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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