Ethyl nipecotate → Ethyl 1-carbamothioylpiperidine-3-carboxylate

HRID 1162603Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].C([N:29]=[C:30]=[S:31])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:30](=[S:31])[NH2:29])[CH2:7]1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 98969Ethyl nipecotate

HCID 4154759Fmoc isothiocyanate

Product 1

HCID 45118651Ethyl 1-carbamothioylpiperidine-3-carboxylateYield 92.5%

Procedure

1-Thiocarbamoyl-piperdine-3-carboxylic acid ethyl ester (400 mg) was prepared following general procedure D using piperdine-3-carboxylic acid ethyl ester (315 mg, 2.0 mmol), and Fmoc-isothiocyanate (562 mg, 2.0 mmol). Purification: (Silica gel, ethyl acetate/hexane 1:1). LCMS m/z 217.0 (M+1)+

Workup

customPurification

Sources & evidence

ORD record: ord-df65ef87250d4afbb91b76b4a7faabdc
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820704B2

Reaction notes

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