Trifluoroacetic acid → HCID 66773665, compound

HRID 1644811Notes

Reaction equation

HRID 1644811 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:19][C:18]([F:21])([F:20])[CH2:17][C@H:16]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=1)=O)(C)(C)C>C(Cl)Cl>[Cl:30][C:26]1[CH:25]=[C:24]([NH:23][CH2:22][C@@H:16]2[CH2:17][C:18]([F:21])([F:20])[CH2:19][NH:15]2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66774596HCID 66774596, compound

Product 1

HCID 66773665HCID 66773665, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to the solution of (S)-2-[(3-chloro-phenylamino)-methyl]-4,4-difluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (0.16 g, 0.0004 mol) in DCM (5 mL) at 0° C. and the reaction mixture was stirred at rt for 12 h. The reaction was monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure using a rotary evaporator and washed with ether (3×10 mL). The crude was basified with sodium bicarbonate and the aqueous layer was extracted with DCM (3×50 mL). The organic layer was dried over anhydrous Na2SO4 and distilled using a rotary evaporator to give the desired (3-chloro-phenyl)-((S)-4,4-difluoro-pyrrolidin-2-ylmethyl)-amine (0.1 g) as a sticky solid.

Workup

  1. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  2. customa rotary evaporator
  3. washwashed with ether (3×10 mL)
  4. extractionthe aqueous layer was extracted with DCM (3×50 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. distillationdistilled
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-3687fd4ab2ea4cfb817f1d3c2829ddb9
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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