Iodine → N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester

HRID 1602012ノート

反応式

HRID 1602012 の反応式
[C:1]([O:5][C:6](=[O:20])[N:7]([C@@H:9]([C:17](=O)[NH2:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].II.[Cl-].[NH4+].[OH-].[Na+]>O1CCCC1.O>[C:1]([O:5][C:6](=[O:20])[N:7]([C@@H:9]([CH2:17][NH2:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

参加物

8

反応物 5

HCID 807IodineHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 54512009N-((1R)-1-carbamoyl-2-phenylethyl)-N-methylcarbamic acid tert.-butylester

生成物 1

HCID 53810010N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester収率 17.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

N-((1R)-1-Carbamoyl-2-phenylethyl)-N-methylcarbamic acid tert.-butylester (2.73 g, 9.81 mmol) was dissolved in tetrahydrofuran (10 ml). The solutioo was cooled to 5° C. A suspension of sodium borohydride (816 mg, 21.58 mmol) in tetrahydrofuran (10 ml) was added. A solution of iodine (1.24 g, 4.91 mmol) was added dropwise. After the addition was completed, the solution was heated to reflux for 16 h. It was cooled to 5° C. A 10% solution of ammonium chloride in water (60 ml) was added dropwise. The solution was warmed to 50° C. for 1 h. It was cooled to room temperature. 1N sodium hydroxide solution was added until pH 14. It was extracted with tert-butyl methyl ether (4×100 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (150 g) using dichloromethane/methanol/25% aqueous ammonia 100:10:1 as eluent to give 453 mg of N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

後処理

  1. additionwas added
  2. additionAfter the addition
  3. temperaturethe solution was heated
  4. temperatureto reflux for 16 h
  5. temperatureIt was cooled to 5° C
  6. temperatureThe solution was warmed to 50° C. for 1 h
  7. temperatureIt was cooled to room temperature
  8. extractionIt was extracted with tert-butyl methyl ether (4×100 ml)
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. customThe solvent was removed in vacuo
  11. customThe crude product was purified by flash chromatography on silica (150 g)

出典と根拠

ORDレコード
ord-14910f9d197e4daf9b006398596a0cd2
出典データセット
uspto-grants-1999_11
特許番号
US05977178

反応ノート

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