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

반응식

HRID 362143 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9878af0257444e9eb8b69125396ea749
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866684

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