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

HRID 2203702Notes

Reaction equation

HRID 2203702 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-9aa3200fedca4796bdae4a1b9f8c6dea
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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