Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → Piperidine-1-carboxamidine

HRID 864498Notes

Reaction equation

HRID 864498 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([NH:43][C:44](=[N:47]C(OCC1C=CC=CC=1)=O)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

Reactant 4

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 178420613HCID 178420613, compoundHCID 178498603HCID 178498603, compound

Product 1

HCID 205051Piperidine-1-carboxamidine

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

  1. customthe synthesis of the analogous compounds where R1
  2. customcondensed with

Sources & evidence

ORD record
ord-cbf7fe583d614752a6c0cf44da7ad4ea
Source dataset
uspto-grants-1996_10
Patent number
US05563158

Reaction notes

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