Sodium borohydride → 3-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-ol

HRID 1946498

反応式

HRID 1946498 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[C:16](=[O:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]2[CH2:22][CH2:21]2)=[CH:6][CH:5]=1>ClCCl.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3[CH:16]([OH:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]2[CH2:21][CH2:22]2)=[CH:8][CH:9]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 584602283-[(4-chlorophenyl)methyl]-2-cyclopropyl-5,6-dihydrocyclopenta[d]imidazol-4(3H)-one

生成物 1

HCID 584602013-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-ol収率 39.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Sodium borohydride (94 mg) was added to a stirred solution of Intermediate 29 (238 mg) in dichloromethane (3 ml) and methanol (3.00 ml). The reaction mixture was stirred for 16 hours. The reaction mixture was concentrated under vacuum, partitioned between EtOAc (20 ml) and water (15 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (2×10 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a dichloromethane:methanol 0-25% gradient. The fractions were combined and concentrated under vacuum. The residue was purified by MDAP (Method B, UV detection only). The solvent was evaporated in vacuo to give the required product (94 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between EtOAc (20 ml) and water (15 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted again with EtOAc (2×10 ml)
  5. customThe phases were separated
  6. customdried (hydrophobic frit)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on silica using a dichloromethane
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by MDAP (Method B, UV detection only)
  11. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-e0b88b8d4939466797f3c091942a60ba
出典データセット
uspto-grants-2013_03
特許番号
US08399444B2

関連ノート

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