Hydrochloric Acid → 4-(6-Azetidin-1-ylpyridin-3-yl)-4-hydroxycyclohexanone

HRID 1025709Notes

Reaction equation

HRID 1025709 reaction equation
[N:1]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3([OH:21])[CH2:20][CH2:19][C:14]4(OCC[O:15]4)[CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[OH-].[Na+]>C1COCC1>[N:1]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3([OH:21])[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]3)=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595561058-[6-(1-Azetidinyl)-3-pyridinyl]-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 595560894-(6-Azetidin-1-ylpyridin-3-yl)-4-hydroxycyclohexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-(6-Azetidin-1-ylpyridin-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol (35 mg) was dissolved in THF (1.2 mL), and then 3 M HCl (0.8 mL) was added at rt. The resulting solution was stirred at rt for 2 h, then basified with 6 N NaOH in ice bath to PH=10. The aqueous layer was extracted with CH2Cl2×3. The combined organic layers were dried, filtered and rotary evaporated to provide 28 mg (97%) of white solid product w/o further purification. MS (M+H+)=247.0.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2×3
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. customrotary evaporated
  5. customto provide
  6. custom28 mg (97%) of white solid product w/o further purification

Sources & evidence

ORD record
ord-006238bf211048e393dba923e9540efa
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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