Trifluoroacetic acid → HCID 22648423, compound

HRID 394002Notes

Reaction equation

HRID 394002 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH2:23])=O)(C)(C)C.FC(F)(F)C(O)=O.CC(OC)(C)C.C1CCCCC1.C(O)C.C(NC(C)C)(C)C>C(Cl)Cl>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[C:16]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH2:23])[CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23533032HCID 23533032, compoundHCID 86591153HCID 86591153, compound

Product 1

HCID 22648423HCID 22648423, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.76 g (4.5 mmole)2-[4-methyl-2-(1-phenyl-vinyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tertiary butylester in 22 ml abs. CH2Cl2 at 0° C. 5.4 ml trifluoroacetic acid are added and the reaction solution is agitated for 1 h at the same temperature. Then the reaction mixture is reduced on the rotary evaporator and the residue is absorbed in 20 ml dichloromethane. The solution is displaced with 20 ml concentrated ammonia solution and the organic phase is separated off. The aqueous phase is extracted twice with 10 ml dichloromethane in each case and the purified organic phases are dried through MgSO4. The solvent is removed on the rotary evaporator and the raw product obtained in this way is cleaned by column chromatography on silica gel with MTBE/cyclohexane/ethanol/diisopropylamine (ratio of volumes=3/1/1+Vo.−%) as the eluant. 1.31 g (4.5 mmole, 100%)2-[4-methyl-2-(1-phenyl-vinyl)-phenoxymethyl]-pyrrolidine are obtained.

Workup

  1. customat 0° C
  2. customThen the reaction mixture is reduced on the rotary evaporator
  3. customthe residue is absorbed in 20 ml dichloromethane
  4. customthe organic phase is separated off
  5. extractionThe aqueous phase is extracted twice with 10 ml dichloromethane in each case
  6. dry with materialthe purified organic phases are dried through MgSO4
  7. customThe solvent is removed on the rotary evaporator
  8. customthe raw product obtained in this way

Sources & evidence

ORD record
ord-e8ccc64f6600490fb78b14fdb5d2d430
Source dataset
uspto-grants-2004_10
Patent number
US06809225B2

Reaction notes

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