Sodium borohydride → 2,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

HRID 29781

反応式

HRID 29781 の反応式
[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[C:3]=1[Br:14].[BH4-].[Na+]>CN(C=O)C.CO>[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10]([OH:11])[C:4]=2[C:3]=1[Br:14]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 686372062,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione

生成物 1

HCID 597892072,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

試薬・触媒・溶媒 1

HCID 21901440N,N-dimethylformamide methanol溶媒

実験手順

To a solution of 2,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione (2.5 g, 7.74 mmol) in a mixture of DMF-MeOH (6 mL) is added NaBH4 (1.47 g, 38.7 mmol). The mixture is stirred at room temperature overnight. It is concentrated and water is added. The mixture is extracted with EtOAc, washed with brine and dried. After the solvent is removed, the residue is subjected to silica gel column chromatography and eluted with CH2Cl2—MeOH to give 2,3-dibromo-4-hydroxy-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one; 1H NMR (DMSO-d6) δ 1.74-1.84 (m, 1H), 2.01-2.10 (m, 1H), 3.00-3.10 (m, 1H), 3.42-3.50 (m, 1H), 4.63-4.68 (m, 1H), 5.06 (d, 1H, J=6.4 Hz), 7.92 (d, 1H, J=4.4 Hz); m/z [M++1] 324.9.

後処理

  1. concentrationIt is concentrated
  2. additionwater is added
  3. extractionThe mixture is extracted with EtOAc
  4. washwashed with brine
  5. customdried
  6. customAfter the solvent is removed
  7. washeluted with CH2Cl2—MeOH

出典と根拠

ORDレコード
ord-e6929fe333de4a2fa482e850fe235ef2
出典データセット
uspto-grants-2008_09
特許番号
US07423031B2

関連ノート

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