1,1-Dichloroethane → Benzyl 4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazine-1-carboxylate

HRID 2239529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239529
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Si:17]([O:24][CH2:25][CH:26]=O)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[Si:17]([O:24][CH2:25][CH2:26][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Komponenten

8

Edukt 5

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 58812409Benzyl 4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazine-1-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of benzyl 1-piperazinecarboxylate (1.751 mL, 9.08 mmol) and 2-(tert-butyldimethylsilyloxy)acetaldehyde (1.209 mL, 9.99 mmol), in MeOH (5 mL) and dichloroethane (5 mL) was stirred for 20 minutes with 4 Å molecular sieves. The mixture was added to a solution of sodium triacetoxyborohydride (4.81 g, 22.70 mmol) in tetrahydrofuran (5 mL) and stirred overnight. The reaction mixture was added to sodium bicarbonate (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were concentrated under reduced pressure, and the residue purified with silica chromatography (EtOAc/MeOH) to give 2.10 g, (61%) of a clear oil. 1H NMR: 7.34 (m, 5H), 5.05 (s, 2H), 3.67 (t, 2H), 3.36 (m, 4H), 2.40 (m, 6H), 0.84 (s, 9H), 0.02 (s, 6H).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. concentrationThe combined organic extracts were concentrated under reduced pressure
  3. customthe residue purified with silica chromatography (EtOAc/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-199a2f879e3b44b5b93082ead199e2e0
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723337B2

Notizen zur Reaktion

Wird geladen…