4-Toluenesulfonyl chloride → HCID 131718419, compound

HRID 1034500Notes

Reaction equation

HRID 1034500 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]2[CH2:17][OH:18])=[O:10])=[CH:5][CH:4]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:18][CH2:17][C@@H:12]2[CH2:13][C@@H:14]([OH:16])[CH2:15][N:11]2[C:9]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=2)=[O:10])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22851794HCID 22851794, compound

Product 1

HCID 131718419HCID 131718419, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-methanol (64 g: 227.6 mmole) in pyridine (350 ml), p-toluenesulfonyl chloride (48 g) is added. The mixture is stirred at room temperature for 4 hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is successively washed with water, dilute hydrochloric acid and aqueous sodium hydrogen carbonate, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-methanol p-toluenesulfonate (60 g). NMR δ(CDCl3) ppm: 2.0 to 2.4(m, 2H), 2.44(s, 3H), 3.3 to 3.7(m, 2H), 3.82(s, 3H), 3.9 to 4.6(m, 4H), 4.8 to 5.1(m, 2H), 6.88(d, J=8.6 Hz, 2H),7.2 to 7.4(m, 4H), 7.6 to 7.8(m, 2 H). IR ν (CHCl3) cm-1 : 3446, 1693.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is successively washed with water, dilute hydrochloric acid and aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b0c65670c0d4d33b077436a373c8a17
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

Loading…