1-Chloro-4-(chloromethyl)benzene → (R)-tert-Butyl (1-(4-chlorobenzyl)pyrrolidin-3-yl)carbamate

HRID 1280942

Reaktionsgleichung

Reaktionsgleichung von HRID 1280942
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.N(CC)(CCC)CCC.[C:19]([O:23][C:24]([NH:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[C:19]([O:23][C:24]([NH:26][CH:27]1[CH2:31][CH2:30][N:29]([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:28]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

5

Edukt 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 519799N,N-DipropylethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Produkt 1

HCID 18426224(R)-tert-Butyl (1-(4-chlorobenzyl)pyrrolidin-3-yl)carbamateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-Chlorobenzyl chloride (4.15 g, 25.8 mmol) and Pr2NEt (6.67 g, 51.6 mmol) were added to a solution of 3-{(tert-butoxycarbonyl)amino}pyrrolidine (4.81 g, 25.8 mmol) in DMF (50 mL). The reaction mixture was stirred at 70° C. for 15 h and the solvent was removed under reduced pressure. Recrystallization (CH3CN, 50 mL) provided the desired material, 3-(tert-butoxycarbonyl)amino-1-(4-chlorobenzyl)pyrrolidine as a pale yellow solid (6.43 g, 80.2%): 1H NMR (CDCl3, 300 MHz) δ1.37 (s, 9 H), 1.5-1.7 (br, 1 H), 2.1-2.4 (m, 2 H), 2.5-2.7 (m, 2 H), 2.83 (br, 1 H), 3.57 (s, 2 H), 4.1-4.3 (br, 1 H), 4.9-5.1 (br, 1 H), 7.15-7.35 (br, 4 H); The purity was determined by RPLC/MS (98%); ESI/MS m/e 311.0 (M++H, C16H24ClN2O2).

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customRecrystallization (CH3CN, 50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-54f1d3fce4e2444bb60cb84022f1d644
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

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