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

HRID 408135Notes

Reaction equation

HRID 408135 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-d84d2814d48b4420aa8743fa6450e7a4
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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