Potassium Carbonate → HCID 11167655, compound

HRID 1387754Notes

Reaction equation

HRID 1387754 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([O:14][CH2:15][CH3:16])[C@H:11]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C@@H:10]([OH:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:26]1[CH:27]=[C:28]([CH2:32][O:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([O:14][CH2:15][CH3:16])[C@H:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:36][CH2:35][CH2:34][O:33][CH2:32][C:28]3[CH:29]=[CH:30][CH:31]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)[C@@H:10]([OH:24])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11450566HCID 11450566, compoundHCID 57057286HCID 57057286, compound

Product 1

HCID 11167655HCID 11167655, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 11.8 g (35.0 mmol) of (3R,4R,5S)-5-ethoxy-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butylester in 40 ml of dimethylformamide was treated in succession with 10.3 g (45.0 mmol) of 3-bromo-propoxymethyl-benzene and 8.29 g (60.0 mmol) of potassium carbonate. This mixture was stirred at 120° C. for 26 hours. Subsequently, it was filtered, concentrated to a few milliliters, poured into 300 ml of an ice/water mixture and extracted three times with 100 ml of dichloromethane each time. The combined organic phases were washed once with a small amount of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The resulting crude product was separated on silica gel using a mixture of dichloromethane and methanol as the eluent and yielded (3R,4R,5S)-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-ethoxy-3-hydroxy-piperidine-1-carboxylic acid tert-butylester as colorless oil; MS: 486 (M+H+); 508 (M+Na+).

Workup

  1. filtrationSubsequently, it was filtered
  2. concentrationconcentrated to a few milliliters
  3. additionpoured into 300 ml of an ice/water mixture
  4. extractionextracted three times with 100 ml of dichloromethane each time
  5. washThe combined organic phases were washed once with a small amount of water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customdried in a high vacuum
  9. customThe resulting crude product was separated on silica gel using
  10. additiona mixture of dichloromethane and methanol as the eluent

Sources & evidence

ORD record
ord-6ed33572c0c447b4ad2d383a57af1100
Source dataset
uspto-grants-2001_07
Patent number
US06268499B1

Reaction notes

Loading…