Trifluoroacetic acid → Tert-butyl 5-[2-(1(rs)-aminopropyl)-4(rs),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(rs)-methylvalerate

HRID 362143

反応式

HRID 362143 の反応式
Cl[CH:2]([B:5]1[O:9][C:8]([CH2:11][CH2:12][CH:13]([CH3:22])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:10])[C:7]([CH3:24])([CH3:23])[O:6]1)[CH2:3][CH3:4].C[Si]([N-:29][Si](C)(C)C)(C)C.[Li+].FC(F)(F)C(O)=O>O1CCCC1>[NH2:29][CH:2]([B:5]1[O:9][C:8]([CH2:11][CH2:12][CH:13]([CH3:22])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:10])[C:7]([CH3:24])([CH3:23])[O:6]1)[CH2:3][CH3:4]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 2733832Lithium HexamethyldisilazideHCID 22619127Tert-butyl 5-[2-(1(rs)-chloropropyl)-4(rs),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(rs)-methylvalerate

生成物 1

HCID 22619085Tert-butyl 5-[2-(1(rs)-aminopropyl)-4(rs),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(rs)-methylvalerate収率 129.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.82 g (2.27 mmol) of tert-butyl 5-[2-(1(RS)-chloropropyl)-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvalerate was dissolved in 10 ml of tetrahydrofuran and then cooledto -78° C. under a nitrogen atmosphere. 2.3 ml (2.3 mmol) of 1M lithium bis(trimethylsilyl)amide in tetrahydrofuran were added dropwise. The solution was then stirred overnight while slowly warming to room temperature. The solvent was removed by evaporation and the residue was taken up in diethyl ether. Insoluble material was removed by filtration and the filtrate was cooled to 0° C. 0.52 ml (6.8 mmol) of trifluoroacetic acid was added and the solution was stirred at 0° C. for 30 minutes. The solution was evaporated and the residue was co-evaporated with toluene to give 1 g of tert-butyl 5-[2-(1(RS)-aminopropyl)-4(RS), 5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvalerate as an oil which was used in the next step without purification.

後処理

  1. customcooledto -78° C. under a nitrogen atmosphere
  2. customThe solvent was removed by evaporation
  3. customInsoluble material was removed by filtration
  4. temperaturethe filtrate was cooled to 0° C
  5. stirringthe solution was stirred at 0° C. for 30 minutes
  6. customThe solution was evaporated

出典と根拠

ORDレコード
ord-9878af0257444e9eb8b69125396ea749
出典データセット
uspto-grants-1999_02
特許番号
US05866684

関連ノート

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