(S)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester → Phenylmethyl(2R)-2-ethyl-1-pyrrolidinecarboxylate

HRID 2367224Notes

Reaction equation

HRID 2367224 reaction equation
[CH3:1][Li].CC1C=CC(S(O[CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])(=O)=O)=CC=1>CCOCC.C(Cl)Cl.[Cu]I>[CH2:14]([C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[CH3:1]

Participants

6

Reactant 2

HCID 10960094(S)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 58504814Phenylmethyl(2R)-2-ethyl-1-pyrrolidinecarboxylateYield 45.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To copper(I) iodide (1.25 g, 6.55 mmol) in Et2O (25 mL) was added methyllithium (8.2 mL, 13.1 mmol) at 0° C. A solution of phenylmethyl(2S)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1-pyrrolidinecarboxylate (0.85 g, 2.182 mmol) in CH2Cl2 (4 mL) was added next, and the reaction mixture was stirred for 2 hours at 0° C. The reaction was quenched with saturated aqueous NH4Cl, and extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 20% EtOAc/hexanes) afforded the title compound (230 mg, 45%) as a colorless oil. LC-MS (ES) m/z=234 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23ab93c781254aa1a5b27c641b2b27da
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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