4-Nitrobenzaldehyde → HCID 58775942, compound

HRID 1715342Notes

Reaction equation

HRID 1715342 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].[CH:26]12[CH2:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][C@@H:27]2[NH2:33].C=O.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[CH:26]12[CH2:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][C@@H:27]2[N:33]([CH3:1])[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 5414-NitrobenzaldehydeHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 12720689(2S)-Bicyclo[2.2.1]heptan-2-amine

Product 1

HCID 58775942HCID 58775942, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (3.5 mmol, 0.75 g) was added to a mixture of 4-nitro-benzaldehyde Compound 4a (2.8 mmol, 0.42 g), (2S)-bicyclo[2.2.1]hept-2-ylamine Compound 15d (3.0 mmol, 0.33 g) and glacial acetic acid (3 drops) in CH2Cl2 (40 mL). The resulting suspension was allowed to stir at room temperature for 12 hrs. An aliquot of the reaction mixture showed the formation of product (MS m/e 247, 100%). An aqueous solution of formaldehyde (37% solution, 9.6 mmol, 0.8 mL) was added to the reaction mixture followed by sodium triacetoxyborohydride (3.5 mmol, 0.75 g) and the mixture was allowed to stir at r.t. for 2 hrs. The reaction mixture was basified with 2N NaOH solution and was extracted with CH2Cl2. The organic layer was washed with brine, separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to obtain (2S)-bicyclo[2.2.1]hept-2-yl-methyl-(4-nitro-benzyl)-amine Compound 15e (0.72 g, 98%) as an orange oil. MS m/e 261 (M+H, 100%), which was used in the next step without further purification.

Workup

  1. stirringto stir at r.t. for 2 hrs
  2. extractionwas extracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. filtrationThe drying agent was filtered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c4cc61e96a2d42b183824fef768ee043
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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