Benzaldehyde → HCID 68534208, compound

HRID 401811Notes

Reaction equation

HRID 401811 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH:9]1[CH2:14][CH:13]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]2=[O:17].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:19]1([CH:18]2[CH:11]3[C:12](=[O:17])[CH:13]4[CH2:15][CH2:16][CH:10]3[CH:9]([CH2:14]4)[NH:8]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 68533409HCID 68533409, compound

Product 1

HCID 68534208HCID 68534208, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A three neck 3 L flask, fitted with a well isolated soxhlet (300 mL) filled with molecular sieves (3 Å), was charged with 5-amino-bicyclo[2.2.2]octan-2-one trifluoro-acetic acid salt (Preparation 76, 85.0 g, 336 mmol, 1.0 eq), benzaldehyde (37.5 mL, 369 mmol, 1.1 eq) and DCM (1.25 L). The suspension was heated to reflux. The clear reaction mixture was concentrated to a tan solid. The latter was suspended in a mixture of diethyl ether (600 mL) and EtOH (50 mL). The solids were collected by filtration (P3) and thoroughly washed with ethyl acetate and diethyl ether. The filter cake was dried in vacuo to yield title compound as an off-white solid (104 g, 305 mmol, 91%, 97.3% pure (HPLC)).

Workup

  1. customA three neck 3 L flask, fitted with a well isolated soxhlet (300 mL)
  2. additionfilled with molecular sieves (3 Å)
  3. temperatureThe suspension was heated to reflux
  4. concentrationThe clear reaction mixture was concentrated to a tan solid
  5. additionThe latter was suspended in a mixture of diethyl ether (600 mL) and EtOH (50 mL)
  6. filtrationThe solids were collected by filtration (P3)
  7. washthoroughly washed with ethyl acetate and diethyl ether
  8. customThe filter cake was dried in vacuo

Sources & evidence

ORD record
ord-174db5b9c3ea43c6b08cab8b19b6f3fd
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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