2-Aminopropanol → Benzyl (2-hydroxy-1-methylethyl)carbamate

HRID 1373500

反応式

HRID 1373500 の反応式
[NH2:1][CH:2]([CH3:5])[CH2:3][OH:4].[C:6](Cl)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(N(CC)CC)C>O1CCCC1.C1(C)C=CC=CC=1>[OH:4][CH2:3][CH:2]([NH:1][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5]

参加物

6

反応物 3

HCID 51262-AminopropanolHCID 8471TriethylamineHCID 10387Benzyl chloroformate

生成物 1

HCID 560855Benzyl (2-hydroxy-1-methylethyl)carbamate収率 79%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In tetrahydrofuran (500 ml) was dissolved 22.53 g (300 mmol) of 2-aminopropanol, and then 155.1 g (300 mmol) of a 30% solution of carbobenzoxy chloride in toluene and a solution of 36.43 g (360 mmol) of triethylamine in tetrahydrofuran were slowly dropped thereinto under ice-cooling. After the resulting mixture was stirred at room temperature for 3 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and diluted hydrochloric acid was added thereto, followed by three runs of extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled to remove the solvent, whereby 49.8 g (yield 79%) of benzyl (2-hydroxy-1-methylethyl)carbamate was obtained.

後処理

  1. temperatureunder ice-cooling
  2. customthe triethylamine hydrochloride precipitated
  3. filtrationwas filtered under reduced pressure
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure and diluted hydrochloric acid
  6. additionwas added
  7. extractionfollowed by three runs of extraction with ethyl acetate
  8. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  9. dry with materialsaturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  10. distillationdistilled
  11. customto remove the solvent

出典と根拠

ORDレコード
ord-9055a548b5d54538a62e5e482c2a0a47
出典データセット
uspto-grants-2007_01
特許番号
US07161032B2

関連ノート

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