Trifluoromethanesulfonic acid → HCID 22671865, compound

HRID 458370Notes

Reaction equation

HRID 458370 reaction equation
[C:1]([O:5][CH2:6][CH:7]1[CH2:12][N:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]([CH2:17][OH:18])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C(=N)O[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C1CCCCC1>[CH2:23]([O:18][CH2:17][CH:10]1[CH2:9][CH2:8][CH:7]([CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:12][N:11]1[S:13]([CH3:16])(=[O:15])=[O:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium BicarbonateHCID 22671871HCID 22671871, compound

Product 1

HCID 22671865HCID 22671865, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

(6-ring): To a solution of (2RS,5RS)-(5-tert-butoxymethyl-1-methanesulfonyl -piperidin-2-yl)-methanol (2.80 g) in dichloromethane (20 ml) and cyclohexane (30 ml) was added benzyl 2,2,2-trichloroacetimidate (3.03 g) and trifluoromethanesulphonic acid (0.2 ml). The reaction mixture was stirred 1 h at room temperature, poured onto a saturated sodium bicarbonate solution and extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:3 and 1:2 as eluents to obtain (2RS,5RS)-2-benzyloxymethyl-5-tert-butoxymethyl-1-methanesulfonyl-piperidine (3,6 g) as a syrup, MS: 369 (M+).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1025a22b5cd14d359de938873afe91c5
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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