4-Toluenesulfonyl chloride → HCID 131732606, compound

HRID 877711Notes

Reaction equation

HRID 877711 reaction equation
[OH:1][C@H:2]1[C@H:6]([O:7][CH3:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.[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>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:8][O:7][C@H:6]1[C@H:2]([O:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:3][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 60128538HCID 60128538, compound

Product 1

HCID 131732606HCID 131732606, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(+/−)-Trans-Benzyl 3-hydroxy-4-methoxypyrrolidine-1-carboxylate (7.7 g, 30.6 mmol) and N,N-dimethylpyridin-4-amine (0.374 g, 3.06 mmol) were dissolved in DCM (75 mL). Cooled to 0 deg. Celsius and added 4-methylbenzene-1-sulfonyl chloride (8.76 g, 46 mmol) and triethylamine (6.41 ml, 46.0 mmol). The reaction was stirred to warm to RT overnight. The solvent was removed and the residue was passed thru a pad of silica to give the product, (+/−)-Trans-benzyl 3-methoxy-4-(tosyloxy)pyrrolidine-1-carboxylate (10.3 g, 25.4 mmol, 83% yield).

Workup

  1. temperatureCooled to 0 deg. Celsius
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-81fcb2fc7c594f3bbea40d37879d98a6
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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