N-Methylpiperidine → HCID 18638245, compound

HRID 1165918Notes

Reaction equation

HRID 1165918 reaction equation
C(OC([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.CN1CC[CH2:27][CH2:26][CH2:25]1.Cl[C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32].[NH2:38][CH2:39][CH:40]1[O:44][N:43]=[C:42]([Br:45])[CH2:41]1>C(Cl)(Cl)Cl>[CH2:34]([O:33][C:31]([N:38]([CH2:39][CH:40]1[O:44][N:43]=[C:42]([Br:45])[CH2:41]1)[C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:11])=[O:32])[C:35]1[CH:37]=[CH:27][CH:26]=[CH:25][CH:36]=1

Participants

6

Reactant 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 14770713HCID 14770713, compound

Product 1

HCID 18638245HCID 18638245, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of N-benzyloxycarbonyl-L-phenylalanine, 0.84 gm, at -20° C. in 50 ml of dry CHCl3, was added N-methyl piperidine, 0.34 ml, with stirring under argon. After 5 minutes, isobutyl chloroformate, 0.36 ml, was added dropwise and after 20 minutes, 5-aminomethyl-3-bromo-4,5-dihydroisoxazole, [optically active [α]D23 =+208.6(CH2Cl2)] 0.5 gm, was added dropwise in 10 ml of dry CHCl3. One hour after the addition, the reaction mixture was brought to room temperature and three hours later, the reaction mixture was washed with 20 ml each of 5% HCl, water, 5% NaHCO3, brine, and dried over anh. MgSO4 and concentrated to give a solid residue. Crystallization from CHCl3 /pentane gave the title compound identical with the most polar isomer obtained in Example 1.

Workup

  1. additionOne hour after the addition
  2. waitthe reaction mixture was brought to room temperature and three hours
  3. washlater, the reaction mixture was washed with 20 ml each of 5% HCl, water, 5% NaHCO3, brine
  4. dry with materialdried over anh. MgSO4
  5. concentrationconcentrated
  6. customto give a solid residue
  7. customCrystallization from CHCl3 /pentane

Sources & evidence

ORD record
ord-8ba3bbb875fc4a4aa9ae92f00c6696e9
Source dataset
uspto-grants-1990_03
Patent number
US04912120

Reaction notes

Loading…