Hydrochloric Acid → HCID 54451470, compound

HRID 975142Notes

Reaction equation

HRID 975142 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH3:22])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1.Cl>C(O)C>[OH:3][CH:4]([CH3:22])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22870334HCID 22870334, compound

Product 1

HCID 54451470HCID 54451470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (423 mg, 11 mol) was added portion-wise over 20 minutes at room temperature, under nitrogen, to a stirred solution of the title compound of Example 37 (1.34 g, 5 mmol) in ethanol (50 ml), then stirring continued for 18 hours. The pH of the resulting reaction mixture was adjusted to 2 with 2N hydrochloric acid, then to 8 with solid sodium carbonate, and the volume reduced to about half by evaporation under reduced pressure, before partitioning between ethyl acetate and water was effected. The organic phase was separated, washed with water, dried (Na2SO4) and evaporated under reduced pressure to give a foam which was purified by column chromatography on silica gel, eluting with a solvent gradient of 0.880 aqueous ammonia:methanol:dichloromethane (0:0:100 to 0:10:90 to 1:10:90 to 1.5:15:85), to afford the title compound as a foam. Rf 0.10 (SS 7). [α]D25 -22° (c=0.1, CH3OH). Found: C,72.07; H,8.96; N,9.56. C17H24N2O; 0.10 CH2Cl2 ; 0.17 H2O requires C,72.34; H,8.71; N,9.87%.

Workup

  1. customThe pH of the resulting reaction mixture
  2. customto 8 with solid sodium carbonate, and the volume reduced to about half by evaporation under reduced pressure
  3. custombefore partitioning between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customto give a foam which
  9. customwas purified by column chromatography on silica gel
  10. washeluting with a solvent gradient of 0.880 aqueous ammonia:methanol:dichloromethane (0:0:100 to 0:10:90 to 1:10:90 to 1.5:15:85)

Sources & evidence

ORD record
ord-84d8544d3d8a4bb98ff598dd23789854
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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