Imidazole → HCID 19914911、化合物

HRID 1090512ノート

反応式

HRID 1090512 の反応式
[CH2:1]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]([CH2:13][O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11206806(1-Benzylpyrrolidine-2,5-diyl)dimethanol

生成物 1

HCID 19914911HCID 19914911、化合物収率 37%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-benzyl-2,5-bis(hydroxymethyl)-pyrrolidine (30 g) and imidazole (27.8 g) in dimethylformamide (300 ml) was added portionwise t-butyldimethylsilyl chloride (20.4 g) at room temperature. After stirring for 1 hour at room temperature, water (0.9 l) and ethyl acetate (1.4 l) was added to the mixture. After shaking, aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with water (3 times) and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V) to give 1-benzyl-5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (16.8 g).

後処理

  1. stirringAfter shaking
  2. customaqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layer was washed with water (3 times) and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customchromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V)

出典と根拠

ORDレコード
ord-f14e9647e01c4174a03bb6a2cbbe376b
出典データセット
uspto-grants-1992_01
特許番号
US05081237

反応ノート

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