Acetic Acid → HCID 22871973, compound

HRID 726863Notes

Reaction equation

HRID 726863 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][CH:10]2[CH:22]=[N:23]O.C(O)C.C(O)(=O)C.[H][H]>O=[Pt]=O.O>[NH2:23][CH2:22][CH:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:15]([CH2:14][CH2:13][C@:11]12[CH3:12])[C@:16]1([CH3:21])[C@H:3]([N:2]([CH3:1])[C:19](=[O:20])[CH2:18][CH2:17]1)[CH2:4][CH2:5]3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 86751696HCID 86751696, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22871973HCID 22871973, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 962WaterSolvent

Procedure

A mixture of (46) (0.67 g, 2.0 mM), ethanol (100 mL), glacial acetic acid (8 mL) and water (4 mL) was reduced in a hydrogen atmosphere (40 p.s.i.) at room temperature in the presence of PtO2 until TLC analysis indicated complete reduction. The filtered reaction mixture was concentrated in vacuo, the residue taken up in chloroform, and the chloroform solution washed with fresh dilute sodium hydrogen carbonate solution and dried (Na2SO4). Concentration of the filtered chloroform solution followed by trituration of the residue obtained with hexane containing a small amount of ether yielded (47) as an off-white solid. MS MH+ calcd for C20H34N2O 318.49, observed m/e 319.

Workup

  1. customThe filtered reaction mixture
  2. concentrationwas concentrated in vacuo
  3. washthe chloroform solution washed with fresh dilute sodium hydrogen carbonate solution
  4. dry with materialdried (Na2SO4)
  5. customobtained with hexane containing a small amount of ether

Sources & evidence

ORD record
ord-a62160e21876444f9bf22a9babde342e
Source dataset
uspto-grants-1998_01
Patent number
US05710275

Reaction notes

Loading…