Tetrabutylammonium Fluoride → HCID 86669236、化合物

HRID 2366860ノート

反応式

HRID 2366860 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[C:15][Si](C)(C)C)=[CH:11][CH:12]=2)[C@H:7]([NH:20][C:21](=[O:26])[O:22][CH:23]([CH3:25])[CH3:24])[CH2:6][C@@H:5]1[CH3:27])(=[O:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH3:25][CH:23]([O:22][C:21](=[O:26])[NH:20][C@H:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=2)[N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([CH3:27])[CH2:6]1)[CH3:24]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 681853971-methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

生成物 1

HCID 86669236HCID 86669236、化合物収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation, see Intermediate 59) (216 mg, 0.559 mmol) in tetrahydrofuran (THF) (3 mL) at room temperature was added TBAF (1M in THF, 0.671 mL, 0.671 mmol) and the resulting black mixture was stirred at this temperature for 35 min. Most of the solvent was removed in vacuo and the residue dissolved in AcOEt. The organic phase was washed with a saturated NaHCO3 aqueous solution then twice with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue on SP4 using a 10 G silica cartridge (Gradient: 13 to 63% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (156 mg, 0.496 mmol, 89% yield) as a very pale yellow foam.

後処理

  1. customat room temperature
  2. customMost of the solvent was removed in vacuo
  3. dissolutionthe residue dissolved in AcOEt
  4. washThe organic phase was washed with a saturated NaHCO3 aqueous solution
  5. dry with materialtwice with brine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue on SP4

出典と根拠

ORDレコード
ord-3cbc084630874d619ab31ba8b6c970fd
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

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