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

HRID 914217ノート

反応式

HRID 914217 の反応式
[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

参加物

8

反応物 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22635306HCID 22635306、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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, 2H) 1.43 (d, J=8 Hz, 1H) 1.47-1.70 (m, 4H) 1.77 (dt, J=12, 6 Hz, 2H) 3.12 (t, J=6 Hz, 1H) 3.19 (t, J=14 Hz, 2H) 3.88 (s, 3H).

後処理

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

出典と根拠

ORDレコード
ord-96143d9f98414f43a7d9eda56ffc2a7d
出典データセット
uspto-grants-2011_09
特許番号
US08026234B2

反応ノート

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