Sodium borohydride → 543713-48-0

HRID 2111676노트

반응식

HRID 2111676 반응식
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1)=O)C>C(O)C>[OH:5][CH2:6][C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10588096Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected

생성물 1

HCID 67284568543713-48-0수율 91.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium borohydride (610 mg, 16 mmol) was added in portions to a solution of 3-ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 1.62 g, 6 mmol) in ethanol (15 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 hours then quenched with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with EtOAc and the organics washed with brine then dried (MgSO4). The solvent was removed by evaporation to give the title compound (1.25 g, 91%). NMR (DMSO): 1.38 (s, 9H), 4.21 (d, 2H), 4.44 (s, 2H), 5.40 (br s, 1H), 6.21 (s, 1H), 7.49 (br s, 1H); m/z 229 (MH)+.

후처리

  1. customthen quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organics washed with brine
  4. dry with materialthen dried (MgSO4)
  5. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-07fe8723aa004bea94974bd30ed18511
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521453B2

반응 노트

불러오는 중…