Hydrochloric Acid → HCID 11731087, compound

HRID 1387756Notes

Reaction equation

HRID 1387756 reaction equation
C(OC([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][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:19][CH:18]=2)[C@@H:10]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)[CH2:9]1)=O)(C)(C)C.Cl>CO>[CH2:28]([O:27][CH2:26][CH2:25][CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:11]2[C@H:12]([O:14][CH2:15][CH3:16])[CH2:13][NH:8][CH2:9][C@@H:10]2[O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:22][CH:21]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11331057HCID 11331057, compound

Product 1

HCID 11731087HCID 11731087, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

14.4 g (23.0 mmol) of (3R,4S,5S)-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-ethoxy-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butylester were placed in 350 ml of abs. methanol at 0° C., then 24 ml (48 mmol) of hydrochloric acid in methanol (2.0 molar) were added dropwise at 5° C. max. and thereafter the mixture was warmed to room temperature. After 120 minutes the reaction mixture was poured into ice-cold sodium hydrogen carbonate solution and the product was extracted three times with dichloromethane, the organic phases were washed once with distilled water, then dried over magnesium sulphate, filtered and concentrated in a water-jet vacuum. The resulting crude product was chromatographed on silica gel with dichloromethane and methanol to yield (3R,4S,5S)-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-ethoxy-3-(naphthalen-2-ylmethoxy)-piperidine as colorless oil; MS: 526(M+H+).

Workup

  1. additionAfter 120 minutes the reaction mixture was poured into ice-cold sodium hydrogen carbonate solution
  2. extractionthe product was extracted three times with dichloromethane
  3. washthe organic phases were washed once with distilled water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in a water-jet vacuum
  7. customThe resulting crude product was chromatographed on silica gel with dichloromethane and methanol

Sources & evidence

ORD record
ord-67b689d0900142818e658df02debb5df
Source dataset
uspto-grants-2001_07
Patent number
US06268499B1

Reaction notes

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