Tert-Butylamine → t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate

HRID 1172258

反応式

HRID 1172258 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[N:3]=1.[C:10]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH2:11][CH2:12][C:13]#[CH:14].C(N)(C)(C)C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[OH:9][CH2:8][C:4]1[N:3]=[C:2]([C:14]#[C:13][CH2:12][CH2:11][C:10]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 6385Tert-ButylamineHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 108773414-Pentynoic acid, 1,1-dimethylethyl ester

生成物 1

HCID 58105203t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate収率 56.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a 200 mL round-bottom flask, 3.49 g of 2-bromopyridine-6-methanol, 3.0 g of t-butyl 4-pentynoate, 190 mg of BHT, 1.17 g of copper(I) iodide, 877 mg of tetrakis(triphenylphosphine)palladium(0), 2.72 g of t-butylamine and 56 mL of DMF were added, and the mixture was stirred under argon atmosphere at 80° C. for 6 hours. After the DMF was removed under reduced pressure from the reaction mixture, saturated aqueous sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=2:1) to give 2.76 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate as a yellow oil.

後処理

  1. customAfter the DMF was removed under reduced pressure from the reaction mixture, saturated aqueous sodium bicarbonate
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-7e5a40fea3f542e6ad4cf74ba32c9a86
出典データセット
uspto-grants-2010_11
特許番号
US07834002B2

関連ノート

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