4-Toluenesulfonyl chloride → 1,1-Dimethylethyl (2S,4R)-4-[[(4-methylphenyl)sulfonyl]oxy]-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate

HRID 1946598Notes

Reaction equation

HRID 1946598 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][OH:15])[CH2:3]1.[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>[S:23]([O:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([CH2:14][O:15][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:3]1)([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 11275979N-Boc-trans-4-hydroxy-L-prolinol

Product 1

HCID 109515041,1-Dimethylethyl (2S,4R)-4-[[(4-methylphenyl)sulfonyl]oxy]-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2S,4R)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (5.40 g, 25.84 mmol) and 4-methylbenzene-1-sulfonyl chloride (14.22 g, 74.6 mmol) were combined in pyridine (50 mL) at 0° C. and store in the refrigerator for 3 days. The reaction mixture was concentrated to half the volume under vacuo and some water (300 mL) was added slowly. The mixture was stirred 1 h until a white solid formed. The solid was filtered and dried on the pump on high-vacuum over night. The solid was recrystallized from MeOH (˜20 ml) and water (few drops) to afford title compound 204 (6.40 g, 49%). LRMS: (calc) 525.15 (found) 426.4 (MH-Boc)+.

Workup

  1. concentrationThe reaction mixture was concentrated to half the volume under vacuo
  2. additionsome water (300 mL) was added slowly
  3. customformed
  4. filtrationThe solid was filtered
  5. customdried on the pump on high-vacuum over night
  6. customThe solid was recrystallized from MeOH (˜20 ml) and water (few drops)

Sources & evidence

ORD record
ord-1ec510b0e4b24230ba51f2755201c443
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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