Diisopropylethylamine → HCID 58790187, compound

HRID 418603Notes

Reaction equation

HRID 418603 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:22][O:21][C:19](=[O:20])[CH2:18][C:17]([NH:2][CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1)=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123460Methyl malonyl chlorideHCID 2756033tert-Butyl 4-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 58790187HCID 58790187, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of tert-butyl 4-aminopiperidine-1-carboxylate hydrochloride (512 mg, 2.16 mmol), methyl 3-chloro-3-oxopropanoate (232 μL, 2.16 mmol), and DIPEA (828 μL, 4.75 mmol) in DCM (20 mL) was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (eluent EtOAc) to afford tert-butyl 4-(3-methoxy-3-oxopropanamido)piperidine-1-carboxylate as a white solid (500 mg, 78%). MS (m/z): 301.1 (M+H). This material (500 mg, 1.67 mmol) was dissolved in MeOH/THF/H2O (2 mL/2 mL/1 mL), and LiOH×H2O (280 mg, 6.75 mmol) was added to the solution. The reaction mixture was stirred for 2 hrs, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (eluent CH3Cl/MeOH/AcOH) to afford the title compound 42 (300 mg, 63% yield) as yellowish syrup. MS (m/z): 287.1 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (eluent EtOAc)

Sources & evidence

ORD record
ord-939bd7dd38a748d29ac311cc2cd567a2
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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