Water → Tert-butyl 4-(1-benzhydrylazetidin-3-yl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 588889ノート

反応式

HRID 588889 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([N:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]2[C:37](OC)=[O:38])[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH:7]([N:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH:25]2[CH2:37][OH:38])[CH2:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 904616531-tert-Butyl 3-methyl 4-(1-benzhydrylazetidin-3-yl)piperazine-1,3-dicarboxylate

生成物 1

HCID 59625963Tert-butyl 4-(1-benzhydrylazetidin-3-yl)-3-(hydroxymethyl)piperazine-1-carboxylate収率 94.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a mixture of LiAlH4 (500 mg, 13.5 mmol) in THF (40 mL) at −40° C. under argon, a solution of 1-tert-butyl 3-methyl 4-(1-benzhydrylazetidin-3-yl)piperazine-1,3-dicarboxylate (1.8 g, 3.87 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred at −5° C. to 5° C. for 1 h and cooled to −20° C. Then water (2 mL) and NaOH (15%) aqueous were added. The resulting mixture was stirred for 15 min. The solid was filtered, and the cake rinsed with ethyl acetate. The combined filtrate was dried over Na2SO4 and concentrated in vacuo to afford the product (1.6 g, 94% yield).

後処理

  1. stirringThe resulting mixture was stirred for 15 min
  2. filtrationThe solid was filtered
  3. washthe cake rinsed with ethyl acetate
  4. dry with materialThe combined filtrate was dried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7fb7f85de40d45fabbaa66fc065015e3
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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