Cyclopentanone → Methyl 3-(cyclopentylamino)-2,2-difluoropropanoate

HRID 1880988노트

반응식

HRID 1880988 반응식
[NH2:1][CH2:2][C:3]([F:9])([F:8])[C:4]([O:6][CH3:7])=[O:5].[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>CCOC(C)=O.CC(O)=O.C1COCC1>[CH:10]1([NH:1][CH2:2][C:3]([F:9])([F:8])[C:4]([O:6][CH3:7])=[O:5])[CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

8

반응물 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22635306HCID 22635306, 화합물

생성물 1

HCID 67117821Methyl 3-(cyclopentylamino)-2,2-difluoropropanoate수율 60%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a round bottom flask was added methyl 3-amino-2,2-difluoropropanoate (570 mg, 3.24 mmol), THF (20 mL), cyclopentanone (0.433 mL, 4.87 mmol), and HOAc (1 mL). To this mixture was added sodium triacetoxyborohydride (1.06 g, 5 mmol) portionwise. The reaction was left to stir overnight. It was then added slowly to a stirring solution of ice, NaHCO3 (sat.), and EtOAc. The aqueous layer was further extracted with EtOAc, the organic extracts combined, dried over MgSO4, filtered and concentrated to yield the desired product as clear syrup (400 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (td, J=13, 6 Hz, 2 H) 1.43 (d, J=8 Hz, 1 H) 1.47-1.70 (m, 4 H) 1.77 (dt, J=12, 6 Hz, 2 H) 3.12 (t, J=6 Hz, 1 H) 3.19 (t, J=14 Hz, 2 H) 3.88 (s, 3 H).

후처리

  1. waitThe reaction was left
  2. extractionThe aqueous layer was further extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9f0a6d534291449cb902740f9761a93d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318727B2

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