Sodium Bicarbonate → 3-[1-(2-Pyridinylmethyl)-2-pyrrolidinyl]phenol

HRID 742578ノート

反応式

HRID 742578 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+]>Br>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 233612632-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine

生成物 1

HCID 233613143-[1-(2-Pyridinylmethyl)-2-pyrrolidinyl]phenol収率 69%

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

実験手順

2-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine and 48% hydrobromic acid (40 ml) were warmed to 100° C. for 7 hrs, cooled to ambient temperature, and neutralized with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane (2 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated to give 2.7 g (69%) of product, mp 96°-98° C.

後処理

  1. extractionThe mixture was extracted with dichloromethane (2 times)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/dichloromethane)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-54121325f6c4430199518ae2bc9af48d
出典データセット
uspto-grants-1996_09
特許番号
US05554750

反応ノート

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