Dichloromethane → 1-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946546노트

반응식

HRID 1946546 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1.ClCCl.[BH4-].[Na+]>CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([OH:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 584602073-[(4-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

생성물 1

HCID 584601671-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol수율 98.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To Intermediate 87 (6.65 g) in a 250 mL round-bottom flask under nitrogen in Methanol (20 mL) and Dichloromethane (DCM) (20 mL) was added sodium borohydride (1.276 g) in three portions (effervescence) and the mixture stirred at room temperature under nitrogen for 16 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The aqueous layer extracted well with ethyl acetate. The combined organics were dried (hydrophobic frit), filtered and evaporated to give the title compound 6.6 g as a white solid. LC/MS MH+397, Rt 2.61 min (5 min run).

후처리

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer extracted well with ethyl acetate
  4. customThe combined organics were dried (hydrophobic frit)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-ec762e1c374c4773b6f4fc2f0cebb631
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399444B2

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