Sodium borohydride → 7-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

HRID 595261노트

반응식

HRID 595261 반응식
[BH4-].[Na+].[O:3]=[C:4]1[CH2:10][CH:9]([CH:11]=[O:12])[C:6]2([CH2:8][CH2:7]2)[NH:5]1>CO.O>[OH:12][CH2:11][CH:9]1[C:6]2([CH2:8][CH2:7]2)[NH:5][C:4](=[O:3])[CH2:10]1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 916185615-Oxo-4-azaspiro[2.4]heptane-7-carbaldehyde

생성물 1

HCID 916184147-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Sodium borohydride (1.4 g, 6.6 mmol) was added to a stirred solution of 5-oxo-4-azaspiro[2.4]heptane-7-carbaldehyde (0.51 g, 3.3 mmol) in methanol (8 mL) and water (12 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4) to give 7-(hydroxymethyl)-4-azaspiro[2.4]heptan-5-one. 1H NMR (400 MHz, CD3OD) δ 3.65-3.42 (m, 2H), 2.73-2.55 (m, 1H), 2.46-2.22 (m, 2H), 1.11-0.92 (m, 1H), 0.83-0.59 (m, 3H).

후처리

  1. dry with materialThe reaction mixture was dried over sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customto afford the crude product residue
  4. customThe crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4)

출처 및 근거

ORD 기록
ord-a153221c65cc478a8b9605a10055c552
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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