Hydrochloric Acid → HCID 67127386, compound

HRID 2422399Notes

Reaction equation

HRID 2422399 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1([N:17]2[CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1.CCOC(C)=O.CCCCCC>CO>[N:17]1([C:7]2([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]2)[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 67127506HCID 67127506, compound

Product 1

HCID 67127386HCID 67127386, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

50 ml 6N hydrochloric acid were added to a solution of 1-(8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-yl)azetidine (10 g) in 100 ml methanol at 0° C. and the reaction mixture was stirred for 1 hour at room temperature. The reaction course was monitored by thin-layer chromatography (75% EtOAc/hexane). Once the conversion was complete the methanol was removed by distillation and the residue was mixed with water (150 ml) and extracted with ethyl acetate (2×100 ml). The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure the residue was taken up in cold water (150 ml) and the solution was stirred for 1 hour and then filtered. The residue that was retained was taken up in ethyl acetate and dried over Na2SO4. Following removal of the solvent under reduced pressure, the desired product (6.5 g, 78%) was obtained in the form of a brown solid.

Workup

  1. customwas removed by distillation
  2. additionthe residue was mixed with water (150 ml)
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customremoval of the solvent under reduced pressure the residue
  6. stirringthe solution was stirred for 1 hour
  7. filtrationfiltered
  8. dry with materialdried over Na2SO4
  9. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b05779e0074b4bd28ee8ea21fa7c7a85
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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