Ethanol → Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate

HRID 1459459ノート

反応式

HRID 1459459 の反応式
C(O)C.Cl.[NH2:5][OH:6].[C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:8].C[O-].[Na+]>O>[NH2:8][C:7](=[N:5][OH:6])[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 4060541Ethyl 4-cyanopiperidine-1-carboxylateHCID 10942334Sodium Methoxide

生成物 1

HCID 54150879Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate収率 47%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Ethanol (150 ml) was added to a solution of hydroxylamine hydrochloride (17.25 g) in water (48 ml). Ethyl 4-cyano-1-piperidinecarboxylate (45 g) was added and the mixture was cooled. Sodium methoxide (44.4 g) was added dropwise at RT and the reaction mixture was stirred for 30 minutes at 60° C. The reaction mixture was cooled, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated, yielding 25 g (40%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate. This fraction was redissolved in 2-propanone and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 22 g (35%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidine-carboxylate hydrochloride (intermediate 2).

後処理

  1. temperaturethe mixture was cooled
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  6. customThe pure fractions were collected
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-09199164904446ca90d349309dcc1eb3
出典データセット
uspto-grants-1998_12
特許番号
US05854261

反応ノート

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