Diethyl Ether → (S)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 2367223Notes

Reaction equation

HRID 2367223 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].CCN(CC)CC.[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C(OCC)C>C(Cl)Cl>[CH3:32][C:31]1[CH:33]=[CH:34][C:28]([S:25]([O:1][CH2:2][C@@H:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])(=[O:27])=[O:26])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

Product 1

HCID 10960094(S)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To phenylmethyl(2S)-2-(hydroxymethyl)-1-pyrrolidinecarboxylate (0.78 g, 3.32 mmol) in CH2Cl2 (10 mL) was added Et3N (0.92 mL, 6.63 mmol) followed by TsCl (0.664 g, 3.48 mmol) and the reaction mixture was stirred overnight at room temperature. The mixture was poured onto water and diethyl ether (Et2O). The aqueous layer was separated and the organic layer was washed with saturated aqueous NaHCO3 followed by brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 20% EtOAc/hexanes) afforded the title compound (0.85 g, 66%) as a colorless oil. LC-MS (ES) m/z=390 [M+H]+.

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with saturated aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4588f93fb6dc4dc0849bc8197f11b854
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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