Cyclopropylamine → 4-[4-(1-Cyclopropylcarbamoyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 409726Notes

Reaction equation

HRID 409726 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([C:22](O)=[O:23])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:27]([CH:31]([CH3:33])[CH3:32])C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1(N)CC1>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]([C:22](=[O:23])[NH:27][CH:31]3[CH2:33][CH2:32]3)[CH3:21])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866861134-[4-(1-Carboxy-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866861144-[4-(1-Cyclopropylcarbamoyl-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3.00 g (9.00 mmol) 4-[4-(1-carboxy-ethyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (IX.1) and 3.85 mL (22.5 mmol) DIPEA in 5 mL DMF, 4.33 g (13.5 mmol) TBTU are added. The mixture is stirred for 15 min at rt. After that time, 0.94 mL (13.5 mmol) cyclopropylamine are added and the mixture is stirred for 12 h at rt. After that time, water is added and the mixture is extracted with EtOAc.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for 12 h at rt
  3. extractionthe mixture is extracted with EtOAc

Sources & evidence

ORD record
ord-df3e0d26be3343afa29854ba35ab927f
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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