Hydrochloric Acid → HCID 54584744, compound

HRID 1442952Notes

Reaction equation

HRID 1442952 reaction equation
C(C1CCC(C)CC1[O:11][C:12]([CH:14]1[CH2:18][CH:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:16][N:15]1C(OC(C)(C)C)=O)=[O:13])(C)C.[ClH:34]>C1(C)C=CC=CC=1>[ClH:34].[F:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][C@@H:17]1[CH2:16][NH:15][C@H:14]([C:12]([OH:13])=[O:11])[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66939726HCID 66939726, compound

Product 1

HCID 54584744HCID 54584744, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(3-Fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2-isopropyl-5-methyl-cyclohexyl)ester (Preparation 35, 0.91 g, 1.96 mmol) was dissolved in toluene (2 ml). 6N hydrochloric acid (50 ml) was added and stirred at reflux for 18 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×20 ml). The aqueous layer was concentrated by evaporated under reduced pressure to give the title compound (417 mg, 81%) as a white solid. 1H-NMR showed a 7:1 ratio of cis:trans diastereoisomers so the product was recrystallised from isopropyl alcohol to give the title compound (170 mg, 65%) in a ratio of 14:1 cis:trans as determined by NMR.

Workup

  1. temperatureat reflux for 18 h
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. concentrationThe aqueous layer was concentrated
  4. customby evaporated under reduced pressure

Sources & evidence

ORD record
ord-233139d657b5424ea28866c7bb30ed13
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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