Triethylamine → (2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine

HRID 1090538ノート

反応式

HRID 1090538 の反応式
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][OH:14])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].C1CCN2C(=NCCC2)CC1>ClCCl.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[O:6])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15086219(2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine

生成物 1

HCID 18639173(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine収率 52%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine (1.0 g) in dichloromethane (15 ml) were added triethylamine (0.7 ml), t-butyldimethylsilyl chloride (0.57 g) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.15 g). The resulting mixture was allowed to stand at ambient temperature for 5 hours. The mixture was diluted with ethyl acetate (150 ml), washed in turn with aqueous ammonium chloride and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (40 ml) eluting with a mixture of n-hexane and ethyl acetate (3:1 V/V) to give (2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine (0.62 g).

後処理

  1. washwashed in turn with aqueous ammonium chloride and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (40 ml)
  5. washeluting with a mixture of n-hexane and ethyl acetate (3:1 V/V)

出典と根拠

ORDレコード
ord-470b413fd5af4a9aa24bd9bff2514ba3
出典データセット
uspto-grants-1992_01
特許番号
US05081237

反応ノート

読み込み中…