4-Amino-1-Boc-piperidine → HCID 66693371, compound

HRID 511080Notes

Reaction equation

HRID 511080 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][N:17]([CH3:19])[NH:16][N:15]=2)=[CH:10][CH:9]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([NH:33][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[NH:18][N:17]([CH3:19])[NH:16][N:15]=3)=[CH:10][CH:9]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 23676156Sodium t-butoxideHCID 66680950HCID 66680950, compound

Product 1

HCID 66693371HCID 66693371, compoundYield 65.9%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium (30 mg; 0.03 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (62 mg; 0.10 mmol), sodium tert-butoxide (240 mg; 2.50 mmol), 5-(4-bromo-phenyl)-1-methyl-1H-tetrazole (406 mg; 1.70 mmol, prepared in accordance with Example 18) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (421 mg; 2.1 mmol) are suspended in dry toluene (7 mL) and the mixture is irradiated in a mono-mode microwave oven for 20 min. at 120° C. The mixture is then cooled down to room temperature, is diluted with ethyl acetate (15 mL), is filtered and is concentrated under reduced pressure. The crude residue is finally purified by chromatography on silica gel (dichloromethane:methanol 100:0 to 98:2) to afford the desired product (401 mg; 1.12 mmol).

Workup

  1. customthe mixture is irradiated in a mono-mode microwave oven for 20 min. at 120° C
  2. filtrationis filtered
  3. concentrationis concentrated under reduced pressure
  4. customThe crude residue is finally purified by chromatography on silica gel (dichloromethane:methanol 100:0 to 98:2)

Sources & evidence

ORD record
ord-7caf8f20c00b4a5e8f9556d3a0393032
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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