Water → 1,3-Pyrrolidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

HRID 2367314노트

반응식

HRID 2367314 반응식
[CH3:1][CH:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH:4]([C:14]([O:16]CC)=[O:15])[CH2:3]1.O[Li].O.O>C1COCC1>[CH3:11][C:10]([O:9][C:7]([N:6]1[CH:2]([CH3:1])[CH2:3][CH:4]([C:14]([OH:16])=[O:15])[CH2:5]1)=[O:8])([CH3:12])[CH3:13]

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19894765HCID 19894765, 화합물

생성물 1

HCID 585047701,3-Pyrrolidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-(1,1-Dimethylethyl) 3-ethyl 5-methyl-1,3-pyrrolidinedicarboxylate (1.0 g, 3.89 mmol, an estimated 3:1 mixture of cis/trans isomers) and LiOH.H2O (228 mg, 5.44 mmol, 1.4 equiv) was stirred in THF (5 mL) and water (2 mL) as a two-phase mixture at room temperature for 18 hours. The mixture was concentrated in vacuo, and the resulting residue was taken up in 15 mL of water, acidified with cold 2N HCl, and extracted with 2×50 mL of EtOAc. The organic were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (1.03 g) as an oil. LC-MS (ES) m/z=230 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with 2×50 mL of EtOAc
  3. dry with materialThe organic were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a98aba7aa71147a7a1821afe8e008a08
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

반응 노트

불러오는 중…