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

HRID 595261ノート

反応式

HRID 595261 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a153221c65cc478a8b9605a10055c552
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

反応ノート

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