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

HRID 1945537

반응식

HRID 1945537 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9865f61559241a29699f22d9698ecf0
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394796B2

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