Benzoic acid, 4-fluoro-, ethyl ester → Ethyl 4-[3-(hydroxymethyl)pyrrolidin-1-yl]benzoate

HRID 2423550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423550
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14]1>>[OH:19][CH2:18][CH:15]1[CH2:16][CH2:17][N:13]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:14]1

Komponenten

3

Edukt 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 13400657(Pyrrolidin-3-yl)methanol

Produkt 1

HCID 57424997Ethyl 4-[3-(hydroxymethyl)pyrrolidin-1-yl]benzoate

Versuchsvorschrift

Ethyl 4-fluorobenzoate and pyrrolidin-3-ylmethanol were coupled following the procedure outlined in example 28 to give ethyl 4-[3-(hydroxymethyl)pyrrolidin-1-yl]benzoate. MS (ESI): 250.0 (M+H). A similar reaction sequence as outlined in example 26 was followed using the above alcohol. 1H NMR (500 MHz, DMSO) δ 12.03 (br s, 1H), 7.76 (d, 2H), 7.25 (d, 1H), 7.21 (d, 1H), 6.89 (d, 1H), 6.56 (d, 2H), 6.38 (d, 1H), 4.05-3.95 (m, 2H), 3.90 (s, 2H), 3.56 (dd, 1H), 3.49-3.42 (m, 1H), 3.38 (dd, 1H), 3.27 (dd, 1H), 2.86-2.78 (m, 1H), 2.77 (t, 2H), 2.26-2.17 (m, 1H), 2.00-1.92 (m, 1H), 1.64-1.53 (m, 2H), 0.92 (s, 9H), 0.91 (t, 3H). MS (ESI): 449.1 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-6c8f338485bd4f1ebafc00be480a80be
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960417B2

Notizen zur Reaktion

Wird geladen…