1,1,1-Trifluoro-N-phenylmethanesulfonamide → Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 1391509Notes

Reaction equation

HRID 1391509 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C1(N[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([O:14][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of t-butyl-4-oxopiperidine-1-carboxylate (6.50 g, 32.6 mmol) in THF (50 mL) was added dropwise to a stirred solution of LDA (24 mL, 35.8 mmol, 1.1 eq., 1.5 M in hexanes) in THF (50 mL) at −78° C. After stirring for 30 min, a solution of N-phenyltrifluoromethanesulfonamide (12.48 g, 35.0 mmol, 1.07 eq.) in THF was added. The reaction mixture was stirred under inert atmosphere for 6 h at 0° C. The reaction was concentrated in vacuo and filtered over a pad of alumina (hexanes/EtOAc 9:1) to afford 2 as a pale yellow oil which was used without further purification (10.26 g, 95%).

Workup

  1. stirringThe reaction mixture was stirred under inert atmosphere for 6 h at 0° C
  2. concentrationThe reaction was concentrated in vacuo
  3. filtrationfiltered over a pad of alumina (hexanes/EtOAc 9:1)

Sources & evidence

ORD record
ord-33a95b3383824f738ff2584a47abbbcf
Source dataset
uspto-grants-2008_03
Patent number
US07338965B2

Reaction notes

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