Trifluoroacetic acid → 1-{1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidin-4-yl}butan-1-one

HRID 333450Notes

Reaction equation

HRID 333450 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:23](=[O:27])[CH2:24][CH2:25][CH3:26])([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:7][C@H:8]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:23](=[O:27])[CH2:24][CH2:25][CH3:26])([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86659316tert-butyl[(R)-2-(4-butyryl-4-cyclohexylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

Product 1

HCID 669876811-{1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidin-4-yl}butan-1-oneYield 110.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 g (2.7 mmol) of tert-butyl[(R)-2-(4-butyryl-4-cyclohexylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate are placed in a mixture composed of 40 mL of DCM and 8 mL of trifluoroacetic acid. The reaction medium is stirred for 2 hours at room temperature and the reaction is then stopped by adding aqueous 1N sodium hydroxide solution. After extracting with dichloromethane, the organic phase is dried over sodium sulfate and then filtered and concentrated. 1.24 g of 1-{1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidin-4-yl}butan-1-one in the form of a colourless oil are obtained in a yield of 100%.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23f686f172f34e6ea6d55ffd461bdad4
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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