Hydrochloric Acid → 4-[(R)-aminophenylmethyl]-1-piperidinecarboxylic acid phenylmethyl ester

HRID 1697283Notes

Reaction equation

HRID 1697283 reaction equation
CC([S@]([NH:7][C@@H:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=O)(C)C.CO.Cl>O1CCOCC1>[NH2:7][C@@H:8]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866632334-[(R)-[[(R)-(1,1-Dimethylethyl)sulfinyl]amino]phenylmethyl]-1-piperidinecarboxylic acid, phenylmethyl ester

Product 1

HCID 666897524-[(R)-aminophenylmethyl]-1-piperidinecarboxylic acid phenylmethyl esterYield 105.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-[(R)-[[(R)-(1,1-dimethylethyl)sulfinyl]amino]phenylmethyl]-1-piperidinecarboxylic acid, phenylmethyl ester (0.59 g), methanol (5 mL) and hydrogen chloride in 1,4-dioxane (4M, 5 mL) was stirred at room temperature for 10 minutes then concentrated in vacuo. The residue was diluted in dichloromethane (2 mL) and triturated with diethyl ether to afford the subtitle compound as a solid (470 mg).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted in dichloromethane (2 mL)
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-d7bb9290769f4a98bb573e792340ad89
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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