Sodium borohydride → Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate

HRID 1945537

反応式

HRID 1945537 の反応式
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:26])[C:7](=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>>[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:18]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

参加物

3

反応物 2

HCID 4311764Sodium borohydrideHCID 59605837Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-ylidene)malonate

生成物 1

HCID 59605280Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate収率 85%

実験手順

To IMS (200 mL) at 0° C., NaBH4 (1.87 g, 0.047 mol) and a solution of 2-(1-(tert-butoxycarbonyl)piperidin-4-ylidene)malonic acid diethyl ester (17 g, 0.050 mol) in IMS (200 mL) were added. The resulting mixture was allowed to warm to ambient temperature and stirred for 1 h, then quenched with water and concentrated in vacuo. The resulting oil was then partitioned between EtOAc and water. The organic layer was separated and washed with brine, then dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow oil (14.6 g, 85%). LCMS (Method H): RT=3.90 min, [M+Na]+ 366.

後処理

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was then partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a9865f61559241a29699f22d9698ecf0
出典データセット
uspto-grants-2013_03
特許番号
US08394796B2

関連ノート

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