Methanol → Methyl 2-(3-azaspiro[5.5]undecan-9-yl)acetate

反応式

O=S(Cl)Cl.C(OC([N:12]1[CH2:17][CH2:16][C:15]2([CH2:22][CH2:21][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH2:18]2)[CH2:14][CH2:13]1)=O)(C)(C)C.[CH3:27]O>>[CH2:16]1[C:15]2([CH2:18][CH2:19][CH:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:21][CH2:22]2)[CH2:14][CH2:13][NH:12][CH2:17]1

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 533023252-{3-[(Tert-butoxy)carbonyl]-3-azaspiro[5.5]undecan-9-yl}acetic acid

生成物 1

HCID 58137329Methyl 2-(3-azaspiro[5.5]undecan-9-yl)acetate

実験手順

Methanol (50 mL) was cooled in an ice bath and SOCl2 (2 mL) was added dropwise with stirring. After 15 min, 2-(3-(tert-butoxycarbonyl)-3-azaspiro[5.5]undecan-9-yl)acetic acid (0.34 g, purchased from WuXi Pharmatech) was added. The mixture was stirred at rt for 2 d and concentrated to afford methyl 2-(3-azaspiro[5.5]undecan-9-yl)acetate as its hydrochloride salt.