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

HRID 870936노트

반응식

HRID 870936 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 84.1%

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 a nitrogen atmosphere was added N-methylmorpholine (0.223 ml, 2.028 mmol) followed by isobutyl chloroformate (0.266 ml, 2.028 mmol) dropwise and stirred for 30 min. The reaction mixture was filtered. The filtrate was added to sodium borohydride (147 mg, 3.87 mmol) in water (10 mL) and stirred for 5 min. The mixture was 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, 1.55 mmol, 84% yield) as a white solid which was taken to the next step without any purification. 1H NMR (400 MHz, CDCl3) δ 3.73-3.59 (m, 3H), 2.24-2.16 (m, 2H), 1.87-1.69 (m, 2H), 1.44 (s, 9H).

후처리

  1. filtrationThe reaction mixture was 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-ac49585f5b50427bb99e1e975351259b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969564B2

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