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Methanol → 2-Amino-4,4,4-trifluorobutan-1-ol

HRID 2275812
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HRID 2275812 반응식
[BH4-].[Li+].Cl[Si](C)(C)C.Cl.[NH2:9][CH:10]([CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](O)=[O:12].CO>C1COCC1>[NH2:9][CH:10]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:11][OH:12]
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참가 물질

6

반응물 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 27565662-Amino-4,4,4-trifluorobutanoic acid hydrochlorideHCID 4148881Lithium borohydride

생성물 1

HCID 534164332-Amino-4,4,4-trifluorobutan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

12.9 ml of 2 M lithium borohydride solution in THF (25.8 mmol, 2.5 equivalents) were initially charged in 20 ml of THF, 6.5 ml of chlorotrimethylsilane (51.1 mmol, 5 equivalents) were added and the mixture was stirred at RT for 5 min. 2.0 g of rac-2-amino-4,4,4-trifluorobutanoic acid hydrochloride (10.3 mmol, 1 equivalent) were then added a little at a time, and the mixture was stirred at RT overnight. 20.4 ml of methanol were then added dropwise, and after the addition had ended the mixture was concentrated. 12 ml of a 20% strength aqueous potassium hydroxide solution were added to the residue, and the mixture was extracted three times with dichloromethane. The combined organic solutions were dried over sodium sulphate, filtered and concentrated. This gave 1.58 g (96% of theory; purity 90%) of the title compound.

후처리

  1. stirringthe mixture was stirred at RT overnight
  2. additionafter the addition
  3. concentrationwas concentrated
  4. addition12 ml of a 20% strength aqueous potassium hydroxide solution were added to the residue
  5. extractionthe mixture was extracted three times with dichloromethane
  6. dry with materialThe combined organic solutions were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cc7fa6f3276c46feb2d96d3b95084fc5
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126998B2

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