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

HRID 1922687

반응식

HRID 1922687 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-e26dcf8e11d7496b9c400226d328faf9
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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