Reaktion #1585070

ord-7bb9c06ce9094c48a2b84f68f7cc8b60

Reaktionsgleichung

CCOC(=O)c1cnc2cc(C3CCN(C(=O)OC(C)(C)C)CC3)ccn12
ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate
[Li+].[OH-]
LiOH
[Cl-].[NH4+]
NH4Cl
→
CC(C)(C)OC(=O)N1CCC(c2ccn3c(C(=O)O)cnc3c2)CC1
7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

Edukte

CCOC(=O)c1cnc2cc(C3CCN(C(=O)OC(C)(C)C)CC3)ccn12
ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate
[Li+].[OH-]
LiOH
[Cl-].[NH4+]
NH4Cl

Reagenzien

Keine

Lösungsmittel

C1CCOC1.CO.O
THF MeOH H2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated

Vorschrift

To a stirring suspension of ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (90) (84 mg, 0.23 mmol) in THF:MeOH:H2O (3:2:1, 1 mL) was added 6N LiOH (0.13 mL). The reaction was stirred at room temperature for 2.5 hours then neutralized with NH4Cl and concentrated to afford 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (91) which was immediately used without purification. MS (m/z) 346.1 (M+1)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09199981B2uspto-grants-2015_12