Carbamate → (1-Aminocyclohexyl)methanol

반응식

C(OC(N)=O)C1C=CC=CC=1.C(OC([NH:22][C:23]1([C:29](O)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=O)C1C=CC=CC=1.C(OC(NC1(CO)CCCCC1)=O)C1C=CC=CC=1.C(=O)([O-])N>>[NH2:22][C:23]1([CH2:29][OH:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

반응물 4

HCID 276Carbamate

HCID 12136Benzyl carbamate

HCID 113578861-(Cbz-amino)cyclohexanecarboxylic acid

HCID 18316421benzyl N-[1-(hydroxymethyl)cyclohexyl]carbamate

생성물 1

HCID 409153(1-Aminocyclohexyl)methanol

실험 절차

1-Amninocyclohexane-1-carboxylic acid was protected as the benzyloxycarbonylamine according to Method B1a, Step 1. 1-(Benzyloxycarbonylamino)cyclohexane-1-carboxylic acid was reduced to 1-(benzyloxycarbonylamino)-1-(hydroxymethyl)cyclohexane according to Method B1a, Step 2. The carbamate was deprotected according to Method B1a, Step 3 to give 1-amino-1-(hydroxymethyl)cyclohexane. The 2-hydroxyethylamine was sequentially treated with SOCl2 and 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.5]decane. The thiazolidine was alkylated with isobutyl bromide according to Method D2b to afford 2-(2-methyl-4-nitrophenylimino)-1-isobutyl-3-thia-1-azaspiro[4.5]decane.