Methane → HCID 59022871、化合物

HRID 1888206ノート

反応式

HRID 1888206 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[Li+].CC([N-]C(C)C)C.CN(OC)[C:21]([CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)=[O:22].[Cl-].[NH4+].C>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[C:6]([C:7]#[N:8])[C:5]([F:10])=[C:4]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[O:22])[CH:3]=1

参加物

8

反応物 5

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27249005-Bromo-2-fluorobenzonitrileHCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

生成物 1

HCID 59022871HCID 59022871、化合物収率 111.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

A solution of 5-bromo-2-fluorobenzonitrile (7.34 g, 36.7 mmols) in dry THF (90 mL) was cooled to −78° C. under a nitrogen atmosphere. A 2M solution of LDA in THF (21.48 mL, 43.0 mmols) was added during 15 mins and the mixture was stirred at −78° C. for 2 h giving a deep blue solution. 1,1-dimethylethyl 4{[methyl(methyloxy)amino]carbonyl}-1-piperidinecarboxylate (12.5 g, 45.9 mmols) in dry THF (45 mL) was added and the reaction mixture was allowed to warm to room temperature and stirred for 16 hrs (overnight). Saturated aqueous ammonium chloride (200 mL) was added followed by ethyl acetate (200 mL). The mixture was treated with charcoal to decolorize, filtered and the organic phase separated. The organic layer was washed with saturated aqueous ammonium chloride and dried over MgSO4. Evaporation of the solvent afforded a green solid (16.8 g). The solid was purified by flash chromatography (Dry loaded onto silica, gradient elution with pentane/ethyl acetate 9:1 v/v to 3:2 v/v) to give the title compound (1.35 g) as a green gum (9%).

後処理

  1. customgiving a deep blue solution
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 hrs (overnight)
  4. filtrationfiltered
  5. customthe organic phase separated
  6. washThe organic layer was washed with saturated aqueous ammonium chloride
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-ea8ab5c4ac7a47a0a500f7e25cbbaae0
出典データセット
uspto-grants-2013_08
特許番号
US08501780B2

反応ノート

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