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

HRID 2387708

반응식

HRID 2387708 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

반응 조건

온도
70 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-013b702c91bc4f508c0d68b0df41921e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268855B2

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