tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate → (2S,3R)-1-tert-Butoxycarbonyl-3-hydroxy-3-(2-methylene-3-phenoxypropyl)-2-phenylpiperidine

HRID 1107275ノート

反応式

HRID 1107275 の反応式
Cl[Mg][CH2:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:5].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH:22]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][C@@:23]([OH:27])([CH2:3][C:4](=[CH2:5])[CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:22]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

参加物

4

反応物 2

HCID 11414684tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylateHCID 178458313HCID 178458313、化合物

生成物 1

HCID 57220489(2S,3R)-1-tert-Butoxycarbonyl-3-hydroxy-3-(2-methylene-3-phenoxypropyl)-2-phenylpiperidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A tetrahydrofluran solution of 3-(chloromagnesio)-2-(phenoxymethyl)-1-propene (0.91M, 3 ml) (Louw et. al. Tetrahedron 48:6087-6104, (1992), prepared from 2.74 mmol of 3-chloro-2-(phenoxymethyl)-1-propene) was slowly added to a solution of (±)1-tert-butoxycarbonyl-2-phenylpiperidin-3-one (Desc. 1) in tetrahydrofuran (3 ml). The solution was stirred at room temperature for 1 hour, quenched by addition of saturated ammonium chloride solution (20 ml) and extracted with ethyl acetate (20 ml). The organic phase was washed (saturated brine), dried (MgSO4), evaporated to a small volume and purified by chromatography on a column containing silica gel (eluting with hexane containing increasing proportions of ethyl acetate between 0% to 20%). Evaporation of the fractions gave the title compound. m/z (CI+)424 (M+H), 324 (M+2H--t-BuOCO--), 368 (M+2H--t-Bu).

後処理

  1. customquenched by addition of saturated ammonium chloride solution (20 ml)
  2. extractionextracted with ethyl acetate (20 ml)
  3. washThe organic phase was washed (saturated brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a small volume
  6. custompurified by chromatography on a column
  7. additioncontaining silica gel (eluting with hexane containing increasing proportions of ethyl acetate between 0% to 20%)
  8. customEvaporation of the fractions

出典と根拠

ORDレコード
ord-31e432fc32e447ab8dc04c3d6c7e32ac
出典データセット
uspto-grants-2000_05
特許番号
US06060469

反応ノート

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