proline dl-form → 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

HRID 457919

反応式

HRID 457919 の反応式
N1CCC[CH:2]1C(O)=O.[C:9]([O:13][C:14]([N:16]1[CH2:20][C:19](=[N:21][O:22][CH3:23])[CH2:18][C@H:17]1[C:24]([OH:26])=[O:25])=[O:15])([CH3:12])([CH3:11])[CH3:10].CO.C[Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1>[CH3:23][O:22][N:21]=[C:19]1[CH2:20][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:15])[C@H:17]([C:24]([O:26][CH3:2])=[O:25])[CH2:18]1

参加物

6

反応物 4

HCID 614proline dl-formHCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

生成物 1

HCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of the oximether- and/or olefin-type 2-pyrrolidinecarboxylic acid intermediate, e.g. (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid (0.648 g, 2.5 mmol), in a 1:1 mixture of methanol and toluene (35 ml) was made. Trimethylsilyl diazomethane (3.8 ml of a 2M solution in hexanes, 7.5 mmol) was then added dropwise to the stirred solution at room temperature under nitrogen. After completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo, and the residue filtered through a pad of silica gel, eluting with ethyl acetate. Removal of solvent from the filtrate gave the methylester product, e.g. 1-tert-butyl 2-methyl(2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate, as a yellow oil (0.646 g, 95% yield).

後処理

  1. customAfter completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo
  2. filtrationthe residue filtered through a pad of silica gel
  3. washeluting with ethyl acetate
  4. customRemoval of solvent from the filtrate

出典と根拠

ORDレコード
ord-d1b970716bbc4b3c94fe462585b988e2
出典データセット
uspto-grants-2007_03
特許番号
US07189754B2

関連ノート

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