Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → Piperidine-1-carboxamidine
Reaction equation
C(N1CCC(CO)CC1)(OC(C)(C)C)=O.OC1C=C(C(OC)=O)ON=1.[N].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C([N:43](C(OCC1C=CC=CC=1)=O)[C:44](=[NH:47])SC)(OCC1C=CC=CC=1)=O>>[C:44]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)(=[NH:43])[NH2:47]Participants
5
Procedure
Scheme XIXb outlines the synthesis of the analogous compounds where R1 is 4-(1-amidinopiperidinyl) instead of 4-amidinophenyl. After initial condensation of N-BOC-4-piperidinylcarbinol with methyl 3-hydroxyisoxazole-5-carboxylate under Mitsunobu conditions, the intermediate ester is saponified and condensed with a 1,3-diaminpropionate using conditions described above. The piperidine nitrogen is deprotected and treated with N,N,-diCBz-S-methylisothiourea to give a protected amidinopiperdine. Hydrogenation gives the amidinopiperidine compounds as the methyl esters. ##STR76##
Workup
- customthe synthesis of the analogous compounds where R1
- customcondensed with
Sources & evidence
- ORD record
- ord-5ee54ec400554d93b8abd8907880ca13
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05691329
Reaction notes
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