4-Toluenesulfonyl chloride → trans-Tert-butyl 4-fluoro-3-(tosyloxy)piperidine-1-carboxylate

HRID 875621Notes

Reaction equation

HRID 875621 reaction equation
[F:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[OH:15].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][C@H:3]1[O:15][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67086934(3R,4R)-1-Boc-4-fluoro-3-piperidinol

Product 1

HCID 131729717trans-Tert-butyl 4-fluoro-3-(tosyloxy)piperidine-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of trans-tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate (3.10 g, 14.1 mmol) and 4-methylbenzene-1-sulfonyl chloride (5.39 g, 28.3 mmol) in pyridine (20 mL) was stirred at room temperature for 18 hours. The pyridine was removed in vacuo, and the residue was dissolved in ethyl acetate (30 mL), washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (hexane:ethyl acetate 2:1) to give trans-tert-butyl 4-fluoro-3-(tosyloxy)piperidine-1-carboxylate (3.95 g, 75%) as a solid.

Workup

  1. customThe pyridine was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified by flash chromatography on silica gel (hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-62ccd8090e9f4393baaf80ca7dfc9b19
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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