Sodium Hydroxide → (S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol

HRID 453818ノート

反応式

HRID 453818 の反応式
C([O:3][C:4]([C@@:6]1([CH3:19])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@@:6]([CH2:4][OH:3])([CH3:19])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66727374(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester

生成物 1

HCID 66727443(S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol収率 93.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester (1.64 g, 6.3 mmol) in dry THF (20 ml) was slowly added to a stirred suspension of LiAlH4 (0.71 g, 18.8 mmol) in dry THF (20 ml) under nitrogen atmosphere. After the addition the mixture was refluxed for 1.5 h. The solution was cooled with an ice bath, stirred vigorously and 2.5 M NaOH was added carefully drop by drop until no reaction occurred and a white precipitate was formed. The solvent was decanted and the solid washed with EtOAc (2×20 ml). The combined organic phases were dried, filtered and evaporated to dryness to give 1.29 g of the alcohol product as a white powder.

後処理

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 1.5 h
  3. temperatureThe solution was cooled with an ice bath
  4. customa white precipitate was formed
  5. customThe solvent was decanted
  6. washthe solid washed with EtOAc (2×20 ml)
  7. customThe combined organic phases were dried
  8. filtrationfiltered
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-b437037f21a144909dde80c77c1fe130
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

反応ノート

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