Potassium;tri(butan-2-yl)boranuide → HCID 69890897、化合物

HRID 2088110ノート

反応式

HRID 2088110 の反応式
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@H:19]([CH:20]=[CH:21][C:22]2=[O:34])[CH2:18]1)#[N:16]>C1COCC1>[C:15]([C@@H:17]1[C@:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@@H:19]([CH2:20][CH2:21][C@H:22]2[OH:34])[CH2:18]1)#[N:16]

参加物

4

反応物 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 69889607HCID 69889607、化合物

生成物 1

HCID 69890897HCID 69890897、化合物収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of K-Selectride® in THF (1M, 6.5 ml, 6.5 mmol) was added dropwise to a stirred solution of (1R*,5S*,7S*)-7-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 23c; 295 mg, 1.11 mmol) in THF (7 ml) at −78° C. The reaction mixture was slowly warm up to +15° C. over 6 hours and carefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml). The mixture was stirred for 20 minutes. The mixture was treated with saturated aqueous Na2SO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (50 mg, 17%).

後処理

  1. temperatureThe reaction mixture was slowly warm up to +15° C. over 6 hours
  2. customcarefully quenched with a mixture of 2M NaOH (8 ml) and H2O2 (35%, 2 ml)
  3. additionThe mixture was treated with saturated aqueous Na2SO3
  4. extractionextracted into dichloromethane
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-28b3c710756042fb9c0aeb8facb00648
出典データセット
uspto-grants-2004_04
特許番号
US06727249B2

反応ノート

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