4-Toluenesulfonyl chloride → HCID 86585070, compound

HRID 1264416Notes

Reaction equation

HRID 1264416 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 70002522HCID 70002522, compound

Product 1

HCID 86585070HCID 86585070, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4.7 g (15.7 mmol) (2S,4R)-4-Hydroxy-2-(piperidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 300 ml CH2Cl2 were treated with 4.5 g (23.6 mmol, 1.5 eq) p-toluene sulfonylchloride in the presence of 2.88 g (23.6 mmol, 1.5 eq) DMAP at RT for 48 h. The solution was washed with 1M KHSO4, water, 5% aq. NaHCO3 solution, water and brine, dried over Na2SO4 and was concentrated. Flash chromatography yielded 6.42 g (90%) (2S,4R)-2-(Piperidine-1-carbonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as white foam.

Workup

  1. washThe solution was washed with 1M KHSO4, water, 5% aq. NaHCO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-3e3ca357a3c34f309fe420a1ecc7b65b
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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