Trifluoroacetic acid → 3-(Pyrrolidin-3-yloxy)pyridine

HRID 412196ノート

反応式

HRID 412196 の反応式
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 10801570tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate

生成物 1

HCID 101542053-(Pyrrolidin-3-yloxy)pyridine収率 30.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 1.3 gm of 3-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-pyridine was added 10 mL of solution containing 5 mL of TFA and 5 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1:0.05, CHCl3:MeOH:conc. NH4OH) to obtain 120 mg (30.4% yield in two steps) of a clear oil: 1H NMR (300 MHz, CD3OD) δ8.21 (1H, d, J=2.6 Hz), 8.11 (1H, d, J=4.7 Hz), 7.38 (2H, m), 5.00 (1H, m), 3.13-2.88 (4H, m), 2.20-1.95 (2H, m); Mass spectrum (ESI) m/z 165.6 (M+H+).

後処理

  1. waitAfter 50 min
  2. customsolvents were removed in vacuo
  3. customthe crude product was purified by flash chromatography (9:1:0.05, CHCl3:MeOH:conc. NH4OH)
  4. customto obtain 120 mg (30.4% yield in two steps) of a clear oil

出典と根拠

ORDレコード
ord-0c39ab77737443c1bb8ef5d05201d4ca
出典データセット
uspto-grants-2003_05
特許番号
US06562847B1

反応ノート

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