HCID 178526011, compound → HCID 178420423, compound

HRID 1960043Notes

Reaction equation

HRID 1960043 reaction equation
C(O)(=O)C(C(C(O)=O)O)O.[CH2:11]([O:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[CH2:23][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[OH-].[Na+]>[CH2:11]([O:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[CH2:23][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 178526011HCID 178526011, compound

Product 1

HCID 178420423HCID 178420423, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred mixture of anhydrous ammonium formate (15.8 g, 0.25 mol) and trans-(S)-2-{(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidin-1-yl}-2-phenylethanol (20.5 g, 0.050 mol) in MeOH (200 mL) is added 10% palladium on carbon (1.00 g), and the resulting mixture is stirred under nitrogen atmosphere at room temperature for 2 hours and then at 35° C. for 3 hours. The reaction mixture is filtered, and the filtrate is concentrated. The crude residue is dissolved with 1N HCl and extracted with ether to remove phenethylalcohol. The water layer is neutrized by addition of 2.5 N NaOH and extracted with CH2Cl2. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated to give crude trans-(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine. To the mixture of crude trans-(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine in EtOH (65 mL), L-tartaric acid (7.60 g, 0.050 mol) is added. The resulting mixture is warmed to 60° C., then cooled slowly to room temperature. The precipitate is filtered and rinsed with additional EtOH to afford trans-(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine tartaric acid salt as off-white crystal. The tartaric acid salt is dissolved in 1N NaOH aq. and extracted with CH2Cl2, and the organic layer is dried over magnesium sulfate, filtered, and evaporated to afford pure trans-(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialthe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f69728d50baf46b68d4aed7e32808f71
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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