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

HRID 718065Notes

Reaction equation

HRID 718065 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-30c5481c5abd4faabdf87a56c5e378c2
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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