Hydrochloric Acid → 5-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 49505

反応式

HRID 49505 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.[CH2:24]([OH:29])[CH2:25][CH2:26][C:27]#[CH:28].Cl>[Cu]I>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:28]#[C:27][CH2:26][CH2:25][CH2:24][OH:29])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 793464-Pentyn-1-ol2 回HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate

生成物 1

HCID 695147945-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester収率 105.9%

試薬・触媒・溶媒 1

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

実験手順

To 3.73 g (12.5 mmol) 5-Bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 25 ml piperidine 722 mg (0.63 mmol) tetrakis-(triphenylphosphine)-palladium and 120 mg (0.625 mmol) CuI were added. The solution was purged with argon and was heated to 80° C. over a period of 45 min, during which 0.9 ml (9.4 mmol) 4-pentynol were added. Additional 0.9 ml (9.4 mmol) 4-pentynol were added and the mixture was stirred for 2 h, poured into ice water and 2M HCl was added. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Purification on silica gel with hexane/EtOAc 4:1 to 2:1 yielded 3.0 g (79%) 5-(5-Hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as light brown solid, MS: 302 (MH+). (See also: Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Teply, Filip; Saman, David; Fiedler, Pavel. Coupling reactions of halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes. Collect. Czech. Chem. Commun. (1999), 64(4), 649-672)

後処理

  1. customThe solution was purged with argon
  2. additionwere added
  3. additionwas added
  4. extractionThe inorganic phase was extracted with ether
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customPurification on silica gel with hexane/EtOAc 4:1 to 2:1

出典と根拠

ORDレコード
ord-6c8d6f9217da4f5a9a94383d8c289b19
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

関連ノート

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