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

HRID 842408

Reaktionsgleichung

Reaktionsgleichung von HRID 842408
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]

Komponenten

5

Edukt 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

Produkt 1

HCID 22619085Tert-butyl 5-[2-(1(rs)-aminopropyl)-4(rs),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(rs)-methylvalerateAusbeute 129,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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 cooled to −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.

Aufarbeitung

  1. temperaturewhile slowly warming to room temperature
  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

Quellen und Nachweise

ORD-Eintrag
ord-62f3901f00514db0bb39c4c0d2a9862c
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372883B1

Verknüpfte Notizen

Wird geladen…