Trifluoroacetic acid → Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate

HRID 1880935ノート

反応式

HRID 1880935 の反応式
C([N:8]([CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(O)C.[OH-].[OH-].[Pd+2]>[CH:9]1([NH:8][CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13]1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 57955532Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate

生成物 1

HCID 57955590Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate収率 88%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

A solution of ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate (2.2 g, 6.8 mmol) in ethanol (20 mL) was hydrogenated with Pd(OH)2 (20%, 240 mg, 0.34 mmol) in presence of TFA (6.8 mmol) at atmospheric pressure for 20 h. The reaction mixture was filtered through celite. The filtrate was concentrated and diluted to EtOAc/H2O, aqueous layer was basified to pH=11-12 by 1N NaOH. The organic layer was then dried and concentrated to give the product (1.38 g, 88%) as light yellow liquid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95 (t, J=7.6 Hz, 3 H) 1.31 (t, J=7.1 Hz, 4 H) 1.41-1.94 (m, 9 H) 2.88-3.08 (m, 3 H) 4.26 (qd, J=7.12, 2.40 Hz, 2 H). [M+H] calc'd for C12H22FNO2, 232; found 232.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted to EtOAc/H2O, aqueous layer
  4. customThe organic layer was then dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4f6e835d6b2431a8253c7b65b283e45
出典データセット
uspto-grants-2012_11
特許番号
US08318727B2

反応ノート

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