Water → (2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

HRID 2217569ノート

反応式

HRID 2217569 の反応式
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:11])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].O.O[Li].O>C(#N)C>[C:15]([O:14][C:12]([N:6]1[CH2:7][C@H:8]([O:10][CH3:11])[CH2:9][C@@H:5]1[C:3]([OH:4])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 541382851-(Tert-butyl) 2-methyl (2R,4R)-4-methoxypyrrolidine-1,2-dicarboxylate

生成物 1

HCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Into a solution of 5 (2.54 g, 9.80 mmol) in acetonitrile (20 mL) was added water (20 mL) and LiOH.H2O (1.64 g, 39.2 mmol). The mixture was stirred at RT for 28 h before removing the acetonitrile under reduced pressure. EtOAc was added to the residue that was then washed with 1N HCl. The aqueous layer was extracted with additional EtOAc and the combined organic layers were washed with brine and dried over MgSO4. The solution was concentrated under reduced pressure to reveal 6 (2.16 g, 90%) as a white solid. MS: APCI (AP−): 244.1 (M)−.

後処理

  1. custombefore removing the acetonitrile under reduced pressure
  2. additionEtOAc was added to the residue that
  3. washwas then washed with 1N HCl
  4. extractionThe aqueous layer was extracted with additional EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationThe solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-61f2c9bda625487ca1bde392b71af730
出典データセット
uspto-grants-2008_08
特許番号
US07407974B2

反応ノート

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