Triethylamine → (3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891718ノート

反応式

HRID 891718 の反応式
Cl.[OH:2][C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[N+:8]([C:11]1[CH:21]=[CH:20][C:14]([CH2:15][O:16][C:17](Cl)=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(N(CC)CC)C>C(Cl)Cl>[OH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:17]([O:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:21][CH:20]=2)=[O:18])[CH2:4]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 2759336(3R)-pyrrolidin-3-ol hydrochloride

生成物 1

HCID 69544008(3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine収率 90.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (3R)-3-hydroxypyrrolidine hydrochloride (7.00 g, 56.6 mmol) in methylene chloride (210 ml) were added chloroformic acid p-nitrobenzyl ester (13.4 g, 62.3 mmol) and triethylamine (17.4 ml, 125 mmol) in an ice bath. The mixture was stirred at room temperature for 5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate as the eluant to afford (3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine (13.6 g, yield 90%) as a pale yellow solid.

後処理

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-013915be61174470b438ae8abf60afdb
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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