(3-bromoprop-1-en-2-yl)benzene → HCID 67440613、化合物

HRID 1664784ノート

反応式

HRID 1664784 の反応式
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:25]>O1CCCC1>[CH3:1][O:2][C:3]([CH:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:9][CH2:10]1)[CH2:25][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:23])=[O:21]

参加物

4

反応物 2

HCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 40429392Benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

生成物 1

HCID 67440613HCID 67440613、化合物収率 77.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hexamethyldisilylazide (1.0 M in THF; 7.31 mL, 7.31 mmol) was added to solution of benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (1.94 g, 6.65 mmol) in tetrahydrofuran (35 mL) at −78° C. After 40 min, [1-(bromomethyl)vinyl]benzene (1.08 mL, 7.31 mmol) was added and the reaction mixture was warmed to ambient temperature. After 18 h, the mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate) gave the title compound (2.11 g). MS 408.2 (M+1).

後処理

  1. waitAfter 18 h
  2. customthe mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-6c8b49e2620d4dc5809317fc8a456a3e
出典データセット
uspto-grants-2011_10
特許番号
US08039460B2

反応ノート

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