3-Chloro-2-methylbenzenesulfonyl chloride → tert-butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate

HRID 656344Notes

Reaction equation

HRID 656344 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]1>C(#N)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

Product 1

HCID 86602353tert-butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3-chloro-2-methylbenzenesulfonyl chloride (0.75 g, 0.0033 mol) in 5 mL of acetonitrile was added to a solution of tert-butyl (3S)-piperidin-3-ylcarbamate (0.67 g, 0.0033 mol) in 5 mL of acetonitrile at 0° C. After stirring at rt for 1.5 h the reaction mixture was filtered and concentrated to afford the desired product, which was used in the next step without further purification.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d70ce23b79a8449cb66dc60591cb0036
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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