1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester → HCID 59191340, compound

HRID 626038Notes

Reaction equation

HRID 626038 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Li]C(CC)C.C([N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=O)(OC(C)(C)C)=O>C1COCC1>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:7]=[CH:6][C:5]([S:2](/[CH:1]=[C:35]3/[NH:34][CH2:38][CH2:37][CH2:36]/3)(=[O:3])=[O:4])=[CH:10][CH:9]=2)=[C:13]([O:20][CH3:21])[CH:14]=1)[CH3:19]

Participants

5

Reactant 3

HCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 59191277HCID 59191277, compoundHCID 178418400CID 53628100

Product 1

HCID 59191340HCID 59191340, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4-ethyl-2-methoxyphenoxy)phenyl methyl sulfone (0.44 mmol; 136 mg), in anhydrous THF (1 mL), under argon, cooled to 0° C., was added sBuLi (1.2M in cyclohexane; 0.89 mmol; 0.74 mL). After stirring for 30 min, a solution of 1-BOC-2-Pyrrolidinone (0.44 mmol; 0.08 mL) in anhydrous THF (1 mL) was slowly added. The reaction was stirred at 0° C. for 30 min. then slowly warmed up to room temperature overnight. The mixture was quenched with water and NH4Cl sat. (3 mL), extracted with ethyl acetate (2*3 mL), to yield a light yellow oil (164 mg), used without further purification.

Workup

  1. stirringThe reaction was stirred at 0° C. for 30 min.
  2. customThe mixture was quenched with water and NH4Cl sat. (3 mL)
  3. extractionextracted with ethyl acetate (2*3 mL)

Sources & evidence

ORD record
ord-09041ad8896d4f459158598cfa912765
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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