Water → (S)-1-Benzyl-3-chloropyrrolidine

HRID 382300

反応式

HRID 382300 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+].O.C(Cl)(Cl)(Cl)[Cl:40]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([Cl:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

生成物 1

HCID 53640613(S)-1-Benzyl-3-chloropyrrolidine収率 72%

実験手順

To a stirred solution of (R)-1-benzyl-3-pyrrolidinol (886 mg, 5.0 mmol) in CCl4 (20 ml) was added triphenylphosphine (1.574 g, 6.0 mmol) at rt. After 20 h stirring at reflux temperature, the solvent was evapolated. Saturated NaHCO3 aqueous solution and water was added to the residue, and the mixture was extracted with AcOEt. The extract was brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1) to give 706 mg (72%) of pale yellow oil.

後処理

  1. temperatureat reflux temperature
  2. extractionthe mixture was extracted with AcOEt
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give brown oil, which
  6. customwas purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1)

出典と根拠

ORDレコード
ord-05a87c677493455388288396b292a2c3
出典データセット
uspto-grants-2001_10
特許番号
US06310061B2

関連ノート

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