Lithium Chloride → [1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

HRID 714629노트

반응식

HRID 714629 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[C:13](OCC)=[O:14].[Cl-].[Li+].[BH4-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>COCCOC>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[CH2:13][OH:14]

참가 물질

6

반응물 4

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 9855836Potassium sodium tartarateHCID 67409298Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate

생성물 1

HCID 67410386[1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

1200 mg (3.5 mmol) of the compound from Example 33A together with 15 mg (0.35 mmol) of lithium chloride were dissolved in 53 ml 1,2-dimethoxyethane, and 198 mg (5.23 mmol) of sodium borohydride were added at 0° C. The mixture was stirred at RT for 1 h. For work-up, 25 ml of a saturated potassium sodium tartrate solution were added with ice cooling and the mixture was extracted with 50 ml of ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1). This gave 800 mg (76% of theory) of the target compound.

후처리

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1)

출처 및 근거

ORD 기록
ord-dd5f10d1e3d04799aab6c5d482bccdb3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187466B2

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