Diisopropylethylamine → HCID 67304739, compound

HRID 535034Notes

Reaction equation

HRID 535034 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH:9]1[C:14]([OH:16])=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][NH:29][CH2:30][CH:31]=2)[CH:23]=[CH:24][CH:25]=1)([CH3:19])[CH3:18].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH:9]1[C:14]([N:29]1[CH2:28][CH:27]=[C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH:17]([CH3:19])[CH3:18])[CH:21]=2)[CH2:31][CH2:30]1)=[O:16])=[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 67304739HCID 67304739, 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-tetrahydro-pyridine (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-25686d4621a245fc8f83700781d74909
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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