HCID 131718785, compound → Hydrochloric Acid

HRID 1595218Notes

Reaction equation

HRID 1595218 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 1 M 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 residue with ethanol and filtration yielded (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 residue was ice cooled and made basic by addition of a sodium hydroxide solution (10 M, approximately 100 ml) and was extracted 5 times with diethyl ether. The combined organic phase was dried and concentrated in vacuo yielding oil, which was distilled in vacuo (70-74° C., mBar) yielding the title compound as clear oil.

Workup

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

Sources & evidence

ORD record
ord-6895e7bc121b448785a0a7cec353d202
Source dataset
uspto-grants-2001_09
Patent number
US06288079B1

Reaction notes

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