Pyrrolidine → 4-Methoxy-5-(pyrrolidin-1-ylmethyl)phenol

HRID 1159421

Reaktionsgleichung

Reaktionsgleichung von HRID 1159421
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl.O>[CH3:11][O:10][C:5]1[C:6]([CH2:7][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 31268PyrrolidineHCID 3583415-Hydroxy-2-MethoxybenzaldehydeHCID 516919Sodium BisulfateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 686208044-Methoxy-5-(pyrrolidin-1-ylmethyl)phenolAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Hydroxy-2-methoxybenzaldehyde (4.5 g, 0.03 mol) was added in portions for 30 min to a mixture of pyrrolidine (3.1 mL, 0.037 mol) and NaB(OAc)3H (7.8 g, 0.037 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 12 h and cooled with an ice bath. Water (50 mL) and 5N NaHSO4 (to pH 1) were added. The organic layer was separated and discarded. The aqueous one was alkalized with saturated K2CO3 to pH 6 and extracted with chloroform (2×50 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (5.42 g, 89%) was obtained as brown crystals. LCMS-data: (M+H)+ 208.1 and 209.1 (calculated for C12H17NO2 207.3). 1H NMR data (DMSO-d6): 8.79 (br. s, 1H ArOH), 6.81 (d, 1H, J=8.1 Hz, Ar—H), 6.74 (d, 1H, J=4.9 Hz, Ar—H); 6.64 (dd, 1H, J1=1.9, J2=8.1, Ar—H), 3.73 (s, 2H, OCH3), 3.42 (s, 2H, ArCH2), 2.33-2.45 (m, 4H, pyrrolidine (CH2)2N), 1.59-1.73 (m, 4H, CH2CH2CH2CH2).

Aufarbeitung

  1. temperaturecooling with an ice bath in an atmosphere of argon
  2. stirringThe mixture was stirred for 12 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionextracted with chloroform (2×50 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8d115a9806714e52b7f4781f3bbe1bd5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812040B2

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