Water → (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179725Notes

Reaction equation

HRID 2179725 reaction equation
CC1[C@@H:8]2[C:9](C)([CH3:10])[C@@H:6]([CH2:7]2)[C:4](=[O:5])[CH:3]=1.C(#N)C.O.CC[O:18][C:19]([CH3:21])=[O:20]>C(Cl)(Cl)(Cl)Cl>[C:4]([C@@H:6]1[CH2:7][C@H:21]([C:19]([OH:18])=[O:20])[C:9]1([CH3:10])[CH3:8])(=[O:5])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 65724Verbenone, (A+-)-

Product 1

HCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of verbenone (about 10 g, 66.57 mmol) in CCl4: ACN: H2O (140 ml) NaIO4 (56.9 g, 266.3 mmol) followed by RuCl3.H2O (catalytic) were added at 0° C. and allowed to stir at room temperature for about 12 hours. After completion of the reaction (monitored by TLC), reaction mixture was diluted with EtOAc (about 200 ml), filtered through celite bed and the organic layer was separated, the aqueous layer extracted with EtOAc (100 ml×2) combined the organic layers dried with Na2SO4 and concentrated under reduced pressure. The resulting crude was stirred in hexane. Solid was filtered and dried under vacuum (8.56 g). 1H NMR (300 MHZ, CDCl3): δ 2.91-2.77 (m, 2H), 2.63 (q, 1H, J=9 Hz), 2.07 (s, 3H), 1.86-1.95 (m, 1H), 1.40 (s, 3H), 0.97 (s, 3H). Mass: [M+1]+ 171 (10%), [M+Na]+ 193 (72%). IR (KBr, cm−1): 3218, 1737, 1694, 1467, 1368, 1283, 1174, 1080, 836, 703. M.R: 109.5° C.-120.7° C.

Workup

  1. additionwere added at 0° C.
  2. customAfter completion of the reaction (monitored by TLC), reaction mixture
  3. filtrationfiltered through celite bed
  4. customthe organic layer was separated
  5. extractionthe aqueous layer extracted with EtOAc (100 ml×2)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. stirringThe resulting crude was stirred in hexane
  9. filtrationSolid was filtered
  10. customdried under vacuum (8.56 g)
  11. custom109.5° C.-120.7° C.

Sources & evidence

ORD record
ord-4aa0a0a5dea04ff98419337d7ad96caa
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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