Hydrochloric Acid → C-(1,4-Dioxa-spiro[4.5]dec-8-yl)-C-(4-methoxy-phenyl)-methylamine

HRID 45212

反応式

HRID 45212 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[O:11]1[C:15]2([CH2:20][CH2:19][CH:18]([C:21]#[N:22])[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1.S([O-])([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+].Cl.[OH-].[Na+]>C1COCC1.COC(C)(C)C.ClCCl>[O:11]1[C:15]2([CH2:20][CH2:19][CH:18]([CH:21]([NH2:22])[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileHCID 178491912HCID 178491912、化合物

生成物 1

HCID 58380923C-(1,4-Dioxa-spiro[4.5]dec-8-yl)-C-(4-methoxy-phenyl)-methylamine

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
0 °C

実験手順

Under argon, 4-methoxy-phenylmagnesium bromide (0.5M in THF, 24 mL, 12 mmol) was added to a solution of 1,4-dioxa-spiro[4.5]decane-8-carbonitrile (1.0 g, 6 mmol) in THF (100 mL). The mixture was stirred under reflux for 16 hours. The reaction mixture was then cooled to 0° C. Saturated sodium sulphate solution was added dropwise until no more precipitate formed. The precipitate was removed by filtration and washed with THF. The combined organic phases were stirred with sodium borohydride (452 mg, 12 mmol) overnight at 25° C. The reaction mixture was then diluted with t-butyl methyl ether (100 mL) and treated with 0.05M aqueous hydrochloric acid (three times with 100 mL). The combined aqueous phases were adjusted to alkaline pH with a 6M aqueous sodium hydroxide solution with cooling, before extraction with dichloromethane gave a solution of the desired product which was used directly in the next stage. Rt=0.74 min (Method 5). Detected mass: 278.2 (M+H+).

後処理

  1. temperatureunder reflux for 16 hours
  2. customformed
  3. customThe precipitate was removed by filtration
  4. washwashed with THF

出典と根拠

ORDレコード
ord-057b2f14c04446eebc113d2a9dff6ddd
出典データセット
uspto-grants-2013_09
特許番号
US08541449B2

関連ノート

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