Sodium borohydride → HCID 131724622、化合物

HRID 393216

反応式

HRID 393216 の反応式
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:5]=1[C:12]#[C:13][CH2:14][N:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][CH2:22][C:23](=[N:36]O)[C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[CH:26][CH:25]=2)[C@@H:17]([C:38]([O:40][CH3:41])=[O:39])[CH2:16]1>CO.[Mo]=O>[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:5]=1[C:12]#[C:13][CH2:14][N:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][CH2:22][CH:23]([NH2:36])[C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[CH:26][CH:25]=2)[C@@H:17]([C:38]([O:40][CH3:41])=[O:39])[CH2:16]1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 136380444methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

生成物 1

HCID 131724622HCID 131724622、化合物収率 45.1%

試薬・触媒・溶媒 2

HCID 139765Molybdenum oxide触媒HCID 887Methanol溶媒

実験手順

1.44 g of sodium borohydride and 0.77 g of molybdenum oxide are added with stirring and under an inert atmosphere, at a temperature in the region of −5° C., to a solution of 2.05 g of methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 100 cm3 of methanol. After 5 hours at a temperature in the region of 20° C., the mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue is purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45μ; mass 30 g), elution being carried out with a dichloromethane/methanol/triethylamine (89/10/1 by volume) mixture. Fractions 3 to 5 (containing the purified product) are combined and then concentrated to dryness under the above conditions. 0.9 g of methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate is obtained.

後処理

  1. concentrationthe mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  2. customThe residue is purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45μ; mass 30 g), elution
  3. additionFractions 3 to 5 (containing the purified product)
  4. concentrationconcentrated to dryness under the above conditions

出典と根拠

ORDレコード
ord-83d7dfc587c34a479d72ffac7d9dc5b1
出典データセット
uspto-grants-2004_10
特許番号
US06806277B2

関連ノート

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