Sodium borohydride → Methyl (3r,4r)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

HRID 393222

反応式

HRID 393222 の反応式
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][C:19](=[N:32]O)[C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)[C@@H:13]([C:34]([O:36][CH3:37])=[O:35])[CH2:12]1>CO.[Mo]=O>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][CH:19]([NH2:32])[C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)[C@@H:13]([C:34]([O:36][CH3:37])=[O:35])[CH2:12]1

参加物

5

反応物 2

HCID 4311764Sodium borohydride2 回HCID 136380445methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

生成物 1

HCID 131724623Methyl (3r,4r)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate収率 36.3%

試薬・触媒・溶媒 2

HCID 139765Molybdenum oxide触媒2 回HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

0.125 g of sodium borohydride and 0.066 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 0.17 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 10 cm3 of methanol. After 5 hours at a temperature in the region of 20° C., 0.125 g of sodium borohydride and 0.066 g of molybdenum oxide are again added and then the reaction mixture is stirred for an additional 18 hours at a temperature in the region of 20° C. The resulting mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is purified by chromatography under a pressure of 50 kPa of nitrogen on a column of silica gel (particle size 20-45 μ; mass 34 g; diameter of the column 2.3 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. Fractions 220 to 365 (containing the purified product) are combined and then concentrated to dryness under the above conditions to afford 0.06 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate.

後処理

  1. concentrationThe resulting mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  2. customThe residue obtained
  3. customis purified by chromatography under a pressure of 50 kPa of nitrogen on a column of silica gel (particle size 20-45 μ
  4. washdiameter of the column 2.3 cm), elution
  5. additionFractions 220 to 365 (containing the purified product)
  6. concentrationconcentrated to dryness under the above conditions

出典と根拠

ORDレコード
ord-88ef3b92c69a48449a38cc2846044888
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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