4-Bromo-4-[bromo(4-methoxycarbonylphenyl)methyl]piperidine-1-carboxylic tert-butyl ester → HCID 10834544, compound

HRID 353437Notes

Reaction equation

HRID 353437 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](Br)([CH:14]([Br:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 105291254-Bromo-4-[bromo(4-methoxycarbonylphenyl)methyl]piperidine-1-carboxylic tert-butyl ester

Product 1

HCID 10834544HCID 10834544, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of compound 4 (5.4 g 11 mmol) in methanol (300 mL) and 2.0 M NaOH (100 mL) was heated at 40° C. for 3 hrs. The solid was collected by filtration, and dried overnight under vacuum. The dry salt was dissolved in 40% acetonitrile/water, and was adjusted to pH 2 using concentrated HCl. The desired product compound 5 (3.8 g, 87%) was isolated as a white powder by filtration: 1H NMR (CDCl3) δ1.45 (s, 9H), 2.22 (dd, J=5.5 Hz, 6.1 Hz, 2H), 2.64 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.34 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.54 (dd, J=5.5 Hz, 6.1 Hz, 2H), 7.35 (d, J=6.7 Hz, 2H), 8.08 (d, J=6.7 Hz, 2H); 13 C NMR (CDCl3) δ28.3, 31.5, 34.2, 44.0, 115.3, 128.7, 129.4 130.3, 137.7, 145.2, 154.6, 170.3.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried overnight under vacuum
  3. dissolutionThe dry salt was dissolved in 40% acetonitrile/water

Sources & evidence

ORD record
ord-4466e2680ab747aeb1d068c0b944a7ef
Source dataset
uspto-grants-2004_06
Patent number
US06753335B2

Reaction notes

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