Diisopropylethylamine → ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate

HRID 333456Notes

Reaction equation

HRID 333456 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].C(N(C(C)C)CC)(C)C.N1C=CC=CC=1O[C:54](=[S:62])OC1C=CC=CN=1>C(Cl)Cl>[CH:23]1([C:15]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17][N:12]([C:10](=[O:11])[C@H:9]([N:8]=[C:54]=[S:62])[CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH2:13][CH2:14]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 66988018ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate trifluoroacetate

Product 1

HCID 86659211ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylateYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 500 mg (0.94 mmol) of ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate trifluoroacetate dissolved in 5 mL of CH2Cl2 and 0.5 mL (2.8 mmol) of diisopropylethylamine are added 219 mg (0.94 mmol) of thiocarbonic acid O,O-bis(2-pyridyl)ester. After stirring the reaction medium for 2 hours at room temperature, the solvents are evaporated off and the crude product obtained is chromatographed on silica gel (eluent: 6/4 heptane/EtOAc). 421 mg of ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate in the form of a colourless oil are obtained in a yield of 97%.

Workup

  1. customthe solvents are evaporated off
  2. customthe crude product obtained
  3. customis chromatographed on silica gel (eluent: 6/4 heptane/EtOAc)

Sources & evidence

ORD record
ord-5826c8f13c4b4e3b96719e85c7bfcc58
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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