Potassium;tri(butan-2-yl)boranuide → HCID 69890897, 화합물

HRID 2088110노트

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HRID 2088110 반응식
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]

참가 물질

4

반응물 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 69889607HCID 69889607, 화합물

생성물 1

HCID 69890897HCID 69890897, 화합물수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-28b3c710756042fb9c0aeb8facb00648
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06727249B2

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