Trimethylsilylacetylene → Methyl-(3-trimethylsilanylethynyl-benzyl)-carbamic acid tert-butyl ester

HRID 17105

反応式

HRID 17105 の反応式
[Si:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].Br[C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>C(N(CC)CC)C.[Cu]I>[C:15]([O:14][C:13](=[O:19])[N:12]([CH3:20])[CH2:11][C:10]1[CH:9]=[CH:8][CH:23]=[C:22]([C:6]#[C:5][Si:1]([CH3:4])([CH3:3])[CH3:2])[CH:21]=1)([CH3:18])([CH3:17])[CH3:16]

参加物

5

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 20738487tert-Butyl 3-bromobenzyl(methyl)carbamate

生成物 1

HCID 60133802Methyl-(3-trimethylsilanylethynyl-benzyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

TMS-Acetylene (2.2 mL, 15.0 mmol) was added dropwise to commercially available tert-butyl 3-bromobenzyl(methyl)carbamate (3.0 g, 10 mmol), CuI (100 mg, 0.5 mmol) and palladium dichlorobistriphenylphosphine (210 mg, 0.3 mmol) in triethylamine (30 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated to 70° C. for 12 hrs before cooling to room temperature and evaporating in vacuo. The residue was triturated with diethyl ether (30 mL), filtered and the filtrate evaporated in vacuo and purified by column chromatography (5% ethyl acetate in hexane) to yield A314.1 (3.2 g, 100%) as a brown oil. HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 2.34 min, M+Na+=340.34

後処理

  1. temperaturebefore cooling to room temperature
  2. customevaporating in vacuo
  3. customThe residue was triturated with diethyl ether (30 mL)
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. custompurified by column chromatography (5% ethyl acetate in hexane)
  7. customto yield A314.1 (3.2 g, 100%) as a brown oil
  8. custom4.6×33 mm (2 min grad)

出典と根拠

ORDレコード
ord-153adfbc9f8a4b9bbf1463520e3cdf53
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

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