Trifluoroacetic acid → Racemic (cis)-4-methoxy-3-methylpiperidine 2,2,2-trifluoroacetate

HRID 80753Notes

Reaction equation

HRID 80753 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][C@H:4]1[CH3:16].[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18]>C(Cl)Cl>[F:20][C:19]([F:22])([F:21])[C:17]([OH:23])=[O:18].[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@H:4]1[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89691688HCID 89691688, compound

Product 1

HCID 89686005Racemic (cis)-4-methoxy-3-methylpiperidine 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of racemic (cis)-tert-butyl 4-methoxy-3-methylpiperidine-1-carboxylate (230 mg, 1.0 mmol) in DCM (2 mL) with TFA (0.23 mL, 3.01 mmol) was stirred at room temperature overnight. The reaction mixture was then concentrated to give racemic (cis)-4-methoxy-3-methylpiperidine 2,2,2-trifluoroacetate. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.27 (s, 3 H), 3.01-3.09 (m, 1 H), 2.93-3.00 (m, 1 H), 2.81-2.93 (m, 1 H), 2.69-2.77 (m, 1 H), 1.90-2.08 (m, 2 H), 1.57-1.67 (m, 1 H), 0.90 (d, J=7.1 Hz, 3 H).

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-033bb99d42374f2c80ff26681f7b8e07
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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