4-Methylmorpholine → (2R,5S)-tert-butyl 2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

HRID 732370ノート

反応式

HRID 732370 の反応式
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@@H:9]1[C:19](O)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][C@@H:9]1[CH2:19][OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 17040153(2R,5S)-1-((tert-butoxy)carbonyl)-5-phenylpyrrolidine-2-carboxylic acid

生成物 1

HCID 68816114(2R,5S)-tert-butyl 2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

To an ice cold solution of commercially available (2R,5S)-5-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.00 g, 3.45 mmol) in 1,2-dimethoxyethane (5 mL) is added 4-methylmorpholine (0.4 mL, 3.795 mmol) and isobutyl chloroformate (0.50 mL, 3.795 mmol). Stir 15 min and filter into cold flask. Add sodium borohydride (0.196 g, 5.17 mmol) in water (3 mL), followed by addition of water (50 mL). Extract product with ethyl acetate (3×50 mL) and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and purify on silica gel to give the title compound (0.886 g, 93%).

後処理

  1. filtrationfilter into cold flask
  2. washExtract product with ethyl acetate (3×50 mL) and wash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. custompurify on silica gel

出典と根拠

ORDレコード
ord-c66594cfc441489289fec32c93fda37d
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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