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

HRID 2367314ノート

反応式

HRID 2367314 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19894765HCID 19894765、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-a98aba7aa71147a7a1821afe8e008a08
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

反応ノート

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