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

HRID 2121868노트

반응식

HRID 2121868 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 21899381Acetic acid--water (1/1)용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-856ec49db9e04f109edccd1f32a87a20
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696476B2

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