4-Toluenesulfonyl chloride → (+/-)-(trans)-Benzyl 3-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate

HRID 877677Notes

Reaction equation

HRID 877677 reaction equation
[OH:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:7][C@H:6]1[C@H:2]([O:1][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:3][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 58277775benzyl (3S,4R)-3-hydroxy-4-methylpyrrolidine-1-carboxylate

Product 1

HCID 131732605(+/-)-(trans)-Benzyl 3-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(+/−)-(trans)-benzyl 3-hydroxy-4-methylpyrrolidine-1-carboxylate (9.2 g, 39.1 mmol) in pyridine (50 mL) at 5° C. was added tosyl chloride (9.69 g, 50.8 mmol) in one portion and the resulting mixture was allowed to warm to rt and stir overnight. The reaction mixture was concentrated and the residue was taken up in dichloromethane (400 mL) and washed with water (50 mL×2), 0.5 N HCl (50 mL×2), water, sat aq. sodium bicarbonate (50 mL×2), brine, then dried over magnesium sulfate, filtered and concentrated to give a dark oil as the crude title compound which was used directly without any further purification. HPLC (method B) retention time=3.60 min. LCMS (m+1)=390.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with water (50 mL×2), 0.5 N HCl (50 mL×2), water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-656cc3aceb0647eba654873c70f90232
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…