Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylate → Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

HRID 278215

反応式

HRID 278215 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[C:16](Br)Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]#[CH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 15503387Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 18187546Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate収率 79.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 118 mg (0.31 mmol) of 1-(t-butoxycarbonyl)-4-(3,3-dibromoprop-2-en-1-yl)piperidine from Step A in THF (4 mL) at −78° C. was added a 2.5M solution of n-butyl lithium (0.370 mL, 0.92 mmol). After stirring at −78° C. for 45 min, the reaction mixture was quenched with sat'd ammonium chloride (4 mL) and diluted with ether (25 mL). After separating the phases, the aqueous layer was extracted with ether. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by FC (4:1 v/v hexanes/ether) to give the title compound (55 mg).

後処理

  1. customthe reaction mixture was quenched with sat'd ammonium chloride (4 mL)
  2. additiondiluted with ether (25 mL)
  3. customAfter separating the phases
  4. extractionthe aqueous layer was extracted with ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by FC (4:1 v/v hexanes/ether)

出典と根拠

ORDレコード
ord-f06c6eac3a3f4a698660b3098e5a9c4b
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

関連ノート

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