Hydrochloric Acid → HCID 178501122, compound

HRID 538074

Reaction equation

HRID 538074 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]=O)([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1)=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(Cl)Cl>[CH3:14][O:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH:25][CH2:11][CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:20][CH2:19]1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 108447642-NitrobenzeneacetaldehydeHCID 178501119HCID 178501119, compound

Product 1

HCID 178501122HCID 178501122, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-Nitro-phenyl)-acetaldehyde (1 g, 5.98 mmol), trans-4-Aminomethyl cyclohexanecarboxylic acid methyl ester hydrogen chloride salt (1.37 g, 6.58 mmol) and TEA (0.92 mL, 6.58 mmol) in dry DCM was stirred at room temperature for 2.5 h. Sodium triacetoxy borohydride (2.53 g, 11.96 mmol) was added and the mixture stirred at room temperature for 25 min. Then (2N) HCl was added until acidic pH and the aqueous layer extracted with DCM. The organic layer was washed with a saturated solution of NaHCO3 and dried over Na2SO4 anhydrous and then evaporated to afford crude product. Finally, the crude product was purified by flash chromatography on silica (ETP/EtOAc 9/1→0/1) to obtain the titled compound (0.51 g, yield: 27%).

Workup

  1. extractionthe aqueous layer extracted with DCM
  2. washThe organic layer was washed with a saturated solution of NaHCO3
  3. dry with materialdried over Na2SO4 anhydrous
  4. customevaporated
  5. customto afford crude product
  6. customFinally, the crude product was purified by flash chromatography on silica (ETP/EtOAc 9/1→0/1)

Sources & evidence

ORD record
ord-46d4c2e571d7477b818f60875b53b2d1
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Linked notes

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