4-Toluenesulfonyl chloride → tert-Butyl (3S)-3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}piperidine-1-carboxylate

HRID 1478603Notes

Reaction equation

HRID 1478603 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[S:16]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 45158786tert-Butyl (3S)-3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}piperidine-1-carboxylateYield 97.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (3.5 g, 16.59 mmol) was dissolved in CH2Cl2 (60 ml), and then TsCl (3.8 g, 19.91 mmol), Et3N (3.47 ml, 24.87 mmol), and DMAP (0.21 g, 1.66 mmol) were added, followed by at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was extracted with H2O, MC, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:5), to give (S)-tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate (6 g, 97%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, MC, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:5)

Sources & evidence

ORD record
ord-91242cf9e43744f5880aeadbe1295309
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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