Sodium Nitrite → (S)-1-(6-Benzyloxyindazol-1-yl)-propan-2-ol

HRID 1815950ノート

反応式

HRID 1815950 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([NH:17][CH2:18][C@@H:19]([OH:21])[CH3:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([CH:13]=[N:22][N:17]2[CH2:18][C@@H:19]([OH:21])[CH3:20])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 23668193Sodium NitriteHCID 867596484-Benzyloxy-2-((S)-2-hydroxy-propylamino)-benzaldehyde

生成物 1

HCID 11659201(S)-1-(6-Benzyloxyindazol-1-yl)-propan-2-ol収率 44.3%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 21899381Acetic acid--water (1/1)溶媒

実験手順

To a mixture of the product from Step C (16.0 g, 56.1 mmol) in acetic acid/water (150 mL/30 mL) at 0° C. was added sodium nitrite (7.75 g, 112 mmol) in portions over 40 min. The mixture was stirred for 50 min, cooled (ice bath), and zinc (14.7 g, 224 mmol) was added in portions. After 1 h the suspension was warmed to room temperature and more zinc was added (14.7 g, 224 mmol). The mixture was stirred for 1 h, concentrated, and extracted with EtOAc (2×300 mL). The extracts were filtered through a filter-aide, and the filtrate was washed with saturated aqueous disodium hydrogen phosphate (to pH 8) and brine, dried, and purifed by chromatrography (silica, 25% EtOAc/hexane) to afford an oil (7.01 g, 44%).

後処理

  1. additionwas added in portions
  2. stirringThe mixture was stirred for 1 h
  3. concentrationconcentrated
  4. extractionextracted with EtOAc (2×300 mL)
  5. filtrationThe extracts were filtered through a filter-aide
  6. washthe filtrate was washed with saturated aqueous disodium hydrogen phosphate (to pH 8) and brine
  7. customdried

出典と根拠

ORDレコード
ord-d56b7286622a413ca3f7bb8667a57f14
出典データセット
uspto-grants-2005_04
特許番号
US06881749B2

反応ノート

読み込み中…