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

HRID 1034631Notes

Reaction equation

HRID 1034631 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-0660f971b0dd47028e16a1326710ce5c
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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