Trifluoroacetic acid → 3-(3,4-Difluorophenyl)pyrrolidin-3-ol

HRID 1931893Notes

Reaction equation

HRID 1931893 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)([OH:13])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:21][C:16]1[CH:15]=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67405004Tert-butyl 3-(3,4-difluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-olYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-3-(3,4-difluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (0.34 g, 1.13 mmol) in dichloromethane (2 mL), was added trifluoroacetic acid (2 mL). The mixture was stirred for 4 h at ambient temperature. The mixture was Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) gave the title compound (0.19 g). MS m/z (relative intensity, 70 eV) 199 (M+, 44), 151 (82), 141 (98), 113 (bp), 63 (99).

Workup

  1. customPurification
  2. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

Sources & evidence

ORD record
ord-648fc7cf37da4e1681fbb7aabad96633
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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