Ammonium Chloride → Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

HRID 61421

反応式

HRID 61421 の反応式
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH4+].[Cl-]>CCOCC>[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 66662569Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate収率 49.24%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in ether (20 ml) was added dropwise phenylmagnesium bromide (10.3 mL, 3.0 M in ether, 6.21 mmol) at rt under nitrogen. The reaction was heated to reflux for 15 min, then cooled to rt, poured into sat. NH4Cl, extracted with ether (3×). The combined organic layers were dried over Na2SO4, concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (700 mg, 49.24%). LCMS (M+H) 264.160.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 min
  3. extractionextracted with ether (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-7420de5697854d5086f76dcd2b4cd9fd
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

関連ノート

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