Sodium cyanoborohydride → N-Methyl-N-((1-methyl-3-nitro-1H-pyrazol-5-yl)methyl)oxetan-3-amine

HRID 1022172ノート

反応式

HRID 1022172 の反応式
[CH3:1][NH:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1.[O:13]1[CH2:16][C:15](=O)[CH2:14]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH3:1][N:2]([CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)[CH:15]1[CH2:16][O:13][CH2:14]1

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 58044304Methyl[(1-methyl-3-nitro-1H-pyrazol-5-YL)methyl]amine

生成物 1

HCID 58043818N-Methyl-N-((1-methyl-3-nitro-1H-pyrazol-5-yl)methyl)oxetan-3-amine収率 80%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 302a (170 mg, 1 mmol) in methanol (4 mL), ZnCl2 (1 mmol/L in diethyl ether) (2 mL, 2 mmol) and oxetan-3-one (150 mg, 2 mmol) were added at room temperature under nitrogen protection, followed by the addition of NaBH3CN (130 mg, 2 mmol). The reaction mixture was warmed to 50° C. and stirred for 3 h. The mixture was then cooled to room temperature and the solvent was removed. The residue was purified on flush column eluting with 50:1 methylene chloride/methanol to afford 302b as a yellow solid (180 mg, 80%, two steps). LCMS: (M+H)+ 227. 1H NMR (500 MHz, DMSO) δ 6.99 (s, 1H), 4.52 (t, J=6.5, 2H), 4.42 (t, J=6, 2H), 3.98 (s, 3H), 3.63 (m, 1H), 3.50 (s, 2H), 2.03 (s, 3H).

後処理

  1. additionwere added at room temperature under nitrogen protection
  2. temperatureThe mixture was then cooled to room temperature
  3. customthe solvent was removed
  4. customThe residue was purified
  5. customon flush column
  6. washeluting with 50:1 methylene chloride/methanol

出典と根拠

ORDレコード
ord-833e96101e494cc29c0b3cf8d0d6f775
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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