4-Methylmorpholine → Tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate

HRID 1398331노트

반응식

HRID 1398331 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[F:16][C:15]([F:17])([F:18])[CH2:14][CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][OH:11]

참가 물질

8

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 534019302-((Tert-butoxycarbonyl)amino)-5,5,5-trifluoropentanoic acid

생성물 1

HCID 86710332Tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate수율 84.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoropentanoic acid (500 mg, 1.843 mmol) in THF (15 mL) cooled to −10° C. under nitrogen atmosphere was added N-methylmorphline (0.223 mL, 2.028 mmol) followed by isobutyl chloroformate (0.266 mL, 2.028 mmol) dropwise. The solution was then stirred for 30 min then filtered. The filtrate was added to sodium borohydride (147 mg, 3.87 mmol) in water (10 mL), stirred for 5 min and diluted with ethyl acetate (10 mL). The organic layer was separated and washed with brine (2×10 mL), dried (Na2SO4) and evaporated under reduced pressure to afford tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate (400 mg, 1.555 mmol, 84% yield) as a white solid which was taken to the next step without further purification. 1H NMR (400 MHz, MeOD) δ 3.44-3.56 (m, 3H), 2.16-2.26 (m, 2H), 1.83-1.92 (m, 1H), 1.57-1.67 (m, 1H), 1.47 (s, 9H).

후처리

  1. filtrationthen filtered
  2. stirringstirred for 5 min
  3. customThe organic layer was separated
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-7064ee34b629441d8a8037c1cf821aad
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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