HCID 131718785, compound → Hydrochloric Acid

HRID 1757138Notes

Reaction equation

HRID 1757138 reaction equation
[ClH:1].[C:2]([C@H:6]1[C@@H:12]([O:13]CC2C=CC=CC=2)[CH2:11][C@H:10]2[N:21]([CH3:22])[C@@H:7]1[CH2:8][CH2:9]2)([O:4]C)=[O:3]>Cl>[OH:13][C@H:12]1[CH2:11][C@H:10]2[N:21]([CH3:22])[C@H:7]([CH2:8][CH2:9]2)[C@H:6]1[C:2]([O-:4])=[O:3].[ClH:1]

Participants

4

Reactant 1

HCID 131718785HCID 131718785, compound

Product 2

HCID 313Hydrochloric AcidHCID 86583652HCID 86583652, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(1R,2R,3S)-2-Carbomethoxy-3-benzoxytropane, hydrochloride (100 g, 0.29 mol) was refluxed in 1000 ml 1M hydrochloric acid for 18 hours and the solution was ice cooled. Benzoic acid was collected by filtration and the filtrate was concentrated in vacuo. Trituration of the remanescens with ethanol and filtration yields (1R,2R,3S)-3-hydroxy-tropane 2 carboxylate, hydrochloride as a white crystalline compound which without further purification was dried and refluxed in phosphorous oxychloride (50 ml) for two hours. The solution was concentrated in vacuo and absolute methanol (150 ml) was slowly added under ice cooling. The solution was stirred at ambient temperature for 16 hours and was concentrated in vacuo. The remanescens was ice cooled and made basic by addition of a sodium hydroxide solution (10M, approximately 100 ml) and was extracted 5 times with diethyl ether. The combined organic phase was dried and concentrated in vacuo yielding an oil, which was distilled in vacuo (70°-74° C., 1 mBar) yielding the title compound as a clear oil.

Workup

  1. temperaturecooled
  2. filtrationBenzoic acid was collected by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. filtrationTrituration of the remanescens with ethanol and filtration

Sources & evidence

ORD record
ord-d5a68fb80652496d9def71813041ed38
Source dataset
uspto-grants-1995_08
Patent number
US05444070

Reaction notes

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