Formaldehyde → HCID 59785882, compound

HRID 1673208Notes

Reaction equation

HRID 1673208 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:25](=[O:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.C=O.N1CCC[CH2:32]1.[BH4-].[Na+]>CCO.CCOC(C)=O.CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([OH:26])[CH:24]([CH3:32])[C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 4311764Sodium borohydrideHCID 24996234HCID 24996234, compound

Product 1

HCID 59785882HCID 59785882, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
65 °C

Procedure

To the product of Example 1 (500 mg, 1.155 mmol) was added paraformaldehyde (347 mL, 11.6 mmol) and pyrrolidine (0.243 mL, 2.94 mmol) in EtOH (10 mL)/THF (3 mL). The reaction vessel was sealed and heated to 65° C. for 4.5 h. The reaction was cooled and diluted with EtOAc and washed with brine. The solution was dried (Na2SO4) and concentrated. The residue was dissolved in THF (8 mL) and MeOH (1 mL) and NaBH4 (87 mg, 2.31 mmol) was added. After 25 min the reaction was diluted with EtOAc and washed with 2 M aq HCl and brine. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-60% EtOAc in hexane affording the title compound. (LC-2) HPLC/MS: 448.2 (M+1), 450.2 (M+3); Rt=4.23 min.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled
  3. washwashed with brine
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in THF (8 mL)
  7. washwashed with 2 M aq HCl and brine
  8. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  9. washeluted with 0-60% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-7edb59d14280493db58497a4d7bcb2fc
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

Loading…