Trifluoroacetic acid → HCID 67506318, compound

HRID 473824Notes

Reaction equation

HRID 473824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@H:12]([OH:14])[CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.ClCCl.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@H:12]([OH:14])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21863450Trifluoroacetic acid methylene chlorideHCID 67506401HCID 67506401, compound

Product 1

HCID 67506318HCID 67506318, compoundYield 158.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To (±)-(2R,4R)-tert-butyl 2-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate (0.10 g, 0.34 mmol) in dichloromethane (10 mL) added trifluoroacetic acid: dichloromethane 1:4 (5 mL) and the mixture was stirred at 25° C. for 30 minutes. The solution was concentrated and dried to give title compound (±)-(2R,4R)-2-(4-fluorophenyl)piperidin-4-ol (105 mg, 99% yield) as the trifluoracetic acid salt. 1H NMR (400 MHz, d6-DMSO): 7.56 (m, 2H), 7.31 (m, 2H), 4.53 (t, 1H), 4.12 (br s, 1H), 3.32 (q, 1H), 3.20 (d, 1H), 2.10 (t, 1H), 1.85 (br d, 2H), 1.79 (dd, 1H). MS (EI) for C11H14FNO: 196 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. customdried

Sources & evidence

ORD record
ord-5592c823bc9243068dd0830c2d9d3545
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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