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

HRID 1855657Notes

Reaction equation

HRID 1855657 reaction equation
[C:1]([C:6]1([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:11][CH2:10][N:9]([C:12](=[O:31])[C@H:13]([NH:23]C(=O)OC(C)(C)C)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:8][CH2:7]1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:23][C@H:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:12]([N:9]1[CH2:10][CH2:11][C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])([CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:7][CH2:8]1)=[O:31]

Participants

5

Reactant 2

HCID 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 86.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.43 g (0.84 mmol) of tert-butyl [(R)-2-(4-butyryl-4-cyclohexylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate is diluted in 8 ml of DCM and 2 ml of trifluoroacetic acid. The solution is stirred for 1 hour 30 minutes at room temperature and then poured into 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried, filtered and then concentrated. 300 mg 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 86%.

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b2774eac25274f289020f0543817a9fe
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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