Sodium Carbonate → HCID 18710240, compound

HRID 278434Notes

Reaction equation

HRID 278434 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C@H:9]([CH2:11]OS(C3C(C)=CC=CC=3)(=O)=O)[CH2:8][C:7]=2[CH:23]=1.[CH3:24][C:25]1[CH:38]=[CH:37][C:28]([CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl.CO>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C@H:9]([CH2:11][N:33]3[CH2:34][CH2:35][C:30]([CH2:29][C:28]4[CH:27]=[CH:26][C:25]([CH3:24])=[CH:38][CH:37]=4)([OH:36])[CH2:31][CH2:32]3)[CH2:8][C:7]=2[CH:23]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 21226129Dichloromethane methanolHCID 88124042(S)-Toluenesulfonic acid 5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl ester

Product 1

HCID 18710240HCID 18710240, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

(S)-Toluenesulfonic acid 5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl ester (2.30g, 6.88 mmol) and 4-(4-methyl-benzyl)-piperidin-4-ol (1.62 g, 7.9 mmol) and Na2CO3 (1.10 g, 10.3 mmol) were suspended in DMF and heated at 110° C. for 1 hr. After cooling to ambient temperature distilled H2O and EtOAc were added (100 ml) and the mixture shaken, the organic phase was then separated and the aqueous phase extracted with EtOAc (10 ml). The combined organic extracts were then washed with satd. NaCl solution (100 ml) and the organic phase dried with Na2SO4, filtered and evaporated to afford a yellow oil. This foam was chromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2, and then with CH2Cl2—MeOH (97:3) to afford (S)-1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (2.20 g, 6.0 mmol, 87% yield) as a yellow oil MS: m/e=368.2 (M+H+) [α]=+45.8° (c=1.0, CHCl3).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. distillationdistilled H2O and EtOAc
  3. additionwere added (100 ml)
  4. customthe organic phase was then separated
  5. extractionthe aqueous phase extracted with EtOAc (10 ml)
  6. washThe combined organic extracts were then washed with satd
  7. dry with materialNaCl solution (100 ml) and the organic phase dried with Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto afford a yellow oil
  11. customThis foam was chromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2

Sources & evidence

ORD record
ord-fa72a7a00fba49be89ec41f6cb2a910c
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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