Sodium borohydride → 1-[(3-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946549노트

반응식

HRID 1946549 반응식
[BH4-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[C:16](=[O:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1>ClCCl.CO>[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[CH:16]([OH:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 584601523-[(3-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

생성물 1

HCID 584601541-[(3-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol수율 97.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

NaBH4 (1.670 g) was added to a stirred solution of Intermediate 90 (5.8 g) in Dichloromethane (DCM) (30 mL) and Methanol (30 mL). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated in vacuo before being partitioned between EtOAc (60 ml) and water (60 ml). The two phases were separated and the aqueous phase was extracted with further EtOAc (2×60 ml). The organic phases were combined, filtered through a hydrophobic frit and concentrated in vacuo to give the desired product (5.7 g) as an off white solid. LC/MS MH+ 397, Rt 2.54 min (5 min run).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custombefore being partitioned between EtOAc (60 ml) and water (60 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with further EtOAc (2×60 ml)
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0734f925938c4f358f2c2726227e8fcb
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399444B2

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