4-Toluenesulfonyl chloride → (3S,4R)-benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylate

HRID 877697Notes

Reaction equation

HRID 877697 reaction equation
[CH2:1]([C@@H:3]1[C@@H:7]([OH:8])[CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1)[CH3:2].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C@@H:3]1[C@@H:7]([O:8][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 46938936(3S,4R)-benzyl 3-ethyl-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86707893(3S,4R)-benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(3S,4R)-benzyl 3-ethyl-4-hydroxypyrrolidine-1-carboxylate (18.9 g, 76 mmol), 4-methylbenzene-1-sulfonyl chloride (21.68 g, 114 mmol) were dissolved in DCM (100 mL) and cooled in an ice bath. Added N,N-dimethylpyridin-4-amine (1.852 g, 15.16 mmol) and triethylamine (11.51 g, 114 mmol) and let the reaction mixture warm to RT overnight. The suspension was passed over a silica column and eluted with Heptanes/EA (9:1 to 4:1 mixtures) to give (3S,4R)-benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylate (28.7 g, 71.1 mmol, 94% yield). LCMS:M+1=404, t=3.07 min.

Workup

  1. temperaturecooled in an ice bath
  2. washeluted with Heptanes/EA (9:1 to 4:1 mixtures)

Sources & evidence

ORD record
ord-dceec6b6e5984d0ba67e142a490a0710
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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