Sodium borohydride → [3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-yl]-methanol

HRID 30485

反応式

HRID 30485 の反応式
C[O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1)=O.[BH4-].[Na+]>CCO>[N:14]1([CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[O:9][N:8]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 445154593-(3-Piperidin-1-yl-propoxy)-isoxazole-5-carboxylic acid methyl ester

生成物 1

HCID 44515460[3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-yl]-methanol収率 99%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 3-(3-piperidin-1-yl-propoxy)-isoxazole-5-carboxylic acid methyl ester (0.200 g, 0.750 mmol) in EtOH (15 mL) was added NaBH4 (0.358 g, 11.2 mmol) was slowly over 30 min. The reaction mixture was heated at reflux overnight, then was cooled to rt and quenched by the addition of 1 N NaOH (10 mL). The mixture was stirred for 1 h, and then was extracted with DCM (3×30 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the desired alcohol (0.177 g, 99%). MS (ESI): exact mass calcd. for C12H20N2O3, 240.15; m/z found, 241.3 [M+H]+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customquenched by the addition of 1 N NaOH (10 mL)
  4. extractionwas extracted with DCM (3×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4fb12e859a844246a266bae6761ac7a9
出典データセット
uspto-grants-2008_09
特許番号
US07423147B2

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