Water → (5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

HRID 590656ノート

反応式

HRID 590656 の反応式
[CH3:1][C@@H:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([C:14]([O:16]CC)=[O:15])[CH2:4][CH2:3]1.O.[OH-].[Li+].O>C(O)C>[C:10]([O:9][C:7]([N:6]1[C@@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:11])([CH3:12])[CH3:13]

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69622155(2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate

生成物 1

HCID 15516206(5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate (6.46 g, 25.1 mmol) in ethanol (20 mL) was added lithium hydroxide mono hydrate (2.11 g, 50.2 mmol) and deionized water (12 mL). The mixture was allowed to stir for 16 hours then partitioned between ethylacetate and a 1:1 mixture of saturated brine and 1N HCl. The aqueous layer was extracted an additional time with ethyl acetate. The organic layers were combined, dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid as a white solid (quant.) and was used directly in the following step.

後処理

  1. customthen partitioned between ethylacetate
  2. additiona 1:1 mixture of saturated brine and 1N HCl
  3. extractionThe aqueous layer was extracted an additional time with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-de03167bdc72435482777e1dba0bdb3d
出典データセット
uspto-grants-2016_01
特許番号
US09233974B2

反応ノート

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