N-Methylpiperidine → HCID 18638245, compound

HRID 1651733Notes

Reaction equation

HRID 1651733 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.C(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

7

Reactant 4

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

Product 1

HCID 18638245HCID 18638245, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

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-cf393eddf2f44079944d9535fef22bfc
Source dataset
uspto-grants-1990_05
Patent number
US04929630

Reaction notes

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