1,2-dibenzyl 3-tert-butyl (2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylate → (2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid

HRID 61428

反応式

HRID 61428 の反応式
[CH3:1][O:2][C:3](=[O:38])[CH:4]=[C:5]1[CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[C@H:8]([C:21]([O:23]CC2C=CC=CC=2)=[O:22])[C@@H:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:6]1.[H][H]>CO.[Pd]>[C:34]([O:33][C:31]([C@H:7]1[CH2:6][CH:5]([CH2:4][C:3]([O:2][CH3:1])=[O:38])[CH2:10][NH:9][C@@H:8]1[C:21]([OH:23])=[O:22])=[O:32])([CH3:37])([CH3:35])[CH3:36]

参加物

5

反応物 2

HCID 866214861,2-dibenzyl 3-tert-butyl (2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67304288(2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid収率 88.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of 1,2-dibenzyl 3-tert-butyl(2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylate (98 mg, 0.188) in methanol (5 mL) was hydrogenated in the presence of 10% palladium on carbon (100 mg, 0.094), under balloon pressure of hydrogen, overnight. The resulting reaction mixture was filtered through a pad of celite and the precipitate was washed with methanol (2×5 mL). The volatiles were removed in-vacuo to afford 50 mg (88%) of (2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid as a sticky amorphous solid, which was used directly in the following coupling without further purification. LCMS (ESI): 246 (M-t-Bu+H+), 302 (M+H+).

後処理

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through a pad of celite
  3. washthe precipitate was washed with methanol (2×5 mL)
  4. customThe volatiles were removed in-vacuo

出典と根拠

ORDレコード
ord-181b7ba947cc412daf16672387dba510
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

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