Trifluoroacetic acid → HCID 22633234, compound

HRID 2417393Notes

Reaction equation

HRID 2417393 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:21]3[CH:16]([C:17]4[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=4[CH2:19][CH2:20]3)[C:15]3[CH:14]=[C:13]([C:26]#[N:27])[CH:12]=[CH:11][C:10]=3[NH:9]2)=[CH:4][C:3]=1[O:28][CH3:29].[BH4-].[Na+].C(O)(C(F)(F)F)=O>C1COCC1>[NH2:27][CH2:26][C:13]1[CH:12]=[CH:11][C:10]2[NH:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:28][CH3:29])[CH:4]=3)[CH:21]3[CH:16]([C:17]4[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=4[CH2:19][CH2:20]3)[C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 22633317HCID 22633317, compound

Product 1

HCID 22633234HCID 22633234, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-(4-Hydroxy-3-methoxy-phenyl)-5,6,6a,7,8,12b-hexahydro-benzo[k]phenanthridine-2-carbonitrile (0.1 mmol; 38.2 mg) was added at 10° C. to a mixture obtained by pre-treating sodium borohydride (600 mg) in 4 mL of THF with a mixture of THF (2 mL) and TFA (1.2 mL). The reaction mixture was reacted overnight before quenching with 1 mL of 10% HCl solution. The mixture was further heated for 1 hour before it was extracted using ammonium hydroxide and water. The organic phase was dried over magnesium sulfate and evaporated to dryness. The residue was purified using HPLC to yield compound 4-(2-Aminomethyl-5,6,6a,7,8,12b-hexahydro-benzo[k]phenanthridin-6-yl)-2-methoxy-phenol. Mass spectrum 369(M−17);in the presence of 0.1M ammonium acetate 385 (M−1) observed for negative ion mode.

Workup

  1. customobtained
  2. customThe reaction mixture was reacted overnight
  3. custombefore quenching with 1 mL of 10% HCl solution
  4. temperatureThe mixture was further heated for 1 hour before it
  5. extractionwas extracted
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified

Sources & evidence

ORD record
ord-71d77c64e16a410b8984cc864742eef6
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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