Diisopropylethylamine → HCID 131737175, compound

HRID 61425Notes

Reaction equation

HRID 61425 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH:9]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]([C:20]1[CH:21]=[C:22]([C:26]2[CH2:27][CH2:28]NCC=2)[CH:23]=[CH:24][CH:25]=1)([CH3:19])[CH3:18].C1CN([P+]([O:48]N2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:65]([N:68]([CH:71](C)C)CC)(C)[CH3:66]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([CH:8]1[CH:13]([C:71]([N:68]2[CH2:65][CH:66]=[CH:28][CH2:27][CH:26]2[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH:17]([CH3:18])[CH3:19])[CH:21]=2)=[O:48])[CH2:12][CH2:11][NH:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 22956954HCID 22956954, compoundHCID 673051604-(3-Isopropyl-phenyl)-1,2,3,6-tetrahydro-pyridine

Product 1

HCID 131737175HCID 131737175, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of piperidine-2,3-dicarboxylic acid 3-tert-butyl ester (100 mg) in DMF (0.6 mL) was added sequentially, 4-(3-isopropyl-phenyl)-1,2,3,6-tetrahydropyridine (97 mg). PyBOP (232 mg), and diisopropylethylamine (0.152 mL). The resultant mixture was stirred at rt overnight. The reaction solution was diluted with EtOAc and washed with saturated NaHCO3 solution (×3), water, and brine. The organic layers were dried over MgSO4, filtered, and concentrated to dry under reduced pressure. The residue was used in next step without further purifications. MS (ESI): 413.2 (M+H+)

Workup

  1. washwashed with saturated NaHCO3 solution (×3), water, and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto dry under reduced pressure

Sources & evidence

ORD record
ord-b9786a318b304490bf004bef6f1818a3
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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