Hydrochloric Acid → (3aR,6aS)-Octahydrocyclopenta[c]pyrrol-5-ol--hydrogen chloride (1/1)

HRID 2367166Notes

Reaction equation

HRID 2367166 reaction equation
CC(OC([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][CH:12]([OH:16])[CH2:13]2)[CH2:9]1)=O)(C)C.[ClH:17]>O1CCOCC1.ClCCCl.C(OCC)C>[CH2:11]1[CH:12]([OH:16])[CH2:13][C@@H:14]2[C@H:10]1[CH2:9][NH:8][CH2:15]2.[ClH:17]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 20753133(Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 67281394(3aR,6aS)-Octahydrocyclopenta[c]pyrrol-5-ol--hydrogen chloride (1/1)

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3.00 g (13.20 mmol) of tert-butyl (3aR,5r,6aS)-5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (see synthesis: WO 2006/108 059) are dissolved in 150 mL of a 2/1 mixture of dioxane and 1,2-dichloroethane. 30 mL (120 mmol) of a 4N solution of hydrogen chloride in dioxane are poured into the medium with stirring. After stirring for 3 hours at room temperature, the medium is concentrated to dryness and the product obtained in hydrochloride form is taken up in diethyl ether for organization of the salt. After filtering off and drying under reduced pressure, 1.745 g (81%) of the expected product are obtained in the form of a hygroscopic solid.

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. concentrationthe medium is concentrated to dryness
  3. customthe product obtained in hydrochloride form
  4. filtrationAfter filtering off
  5. dry with materialdrying under reduced pressure, 1.745 g (81%) of the expected product
  6. customare obtained in the form of a hygroscopic solid

Sources & evidence

ORD record
ord-4d1494385ebc4c37be8a521a83e13e0f
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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