(Dimethyl sulfide)trihydroboron → HCID 57444163、化合物

HRID 875154

反応式

HRID 875154 の反応式
[ClH:1].[CH3:2][C@:3]([NH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=O.CSC.B>C1COCC1>[ClH:1].[ClH:1].[CH3:2][C@:3]([NH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57444166(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine hydrochloride

生成物 1

HCID 57444163HCID 57444163、化合物収率 156.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under an argon atmosphere 412 mg of (1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine hydrochloride (1.522 mmol) were dissolved in 30 mL of dry THF. A 2 M solution of borane dimethylsulfide (4.4 mL, 5.78 mmol) was added dropwise at 0° C. and the mixture stirred for 10 minutes at 0° C. and then allowed to reach room temperature (gas evolution). After 4 hours the reaction was quenched with methanol (added very carefully) and diluted with methanol when effervescence ceased. THF was removed under vacuo and the methanolic solution was heated at 60° C. for 30 minutes. The solvent was at last completely removed recovering 330 mg of the amine that was subsequently dissolved in 15 mL of dioxane and treated with 1.35 mL of HCl 4 N in dioxane. After 1 hour the solvent was evaporated and the product was triturated with diethylether to yield 350 mg of the expected salt.

後処理

  1. customto reach room temperature
  2. customAfter 4 hours the reaction was quenched with methanol (
  3. additionadded very carefully) and
  4. additiondiluted with methanol when effervescence
  5. customTHF was removed under vacuo
  6. temperaturethe methanolic solution was heated at 60° C. for 30 minutes
  7. customcompletely removed
  8. customrecovering 330 mg of the amine that
  9. dissolutionwas subsequently dissolved in 15 mL of dioxane
  10. additiontreated with 1.35 mL of HCl 4 N in dioxane
  11. customAfter 1 hour the solvent was evaporated
  12. customthe product was triturated with diethylether

出典と根拠

ORDレコード
ord-e86062fdecf54ccf924ef341fd5358d1
出典データセット
uspto-grants-2015_03
特許番号
US08981089B2

関連ノート

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