Nitrogen → Methyl (3β)-3-hydroxy-7-oxochol-5-en-24-oate

HRID 234726Notes

Reaction equation

HRID 234726 reaction equation
C([O-])([O-])=O.[K+].[K+].C([O:10][C@H:11]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C:13](=[CH:14][C:15](=[O:38])[C@@H:16]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:37])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@H:21]([CH3:28])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:12]1)(=O)C.N#N>CO>[OH:10][C@H:11]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C:13](=[CH:14][C:15](=[O:38])[C@@H:16]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:37])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@H:21]([CH3:28])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:12]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 23250093HCID 23250093, compound

Product 1

HCID 23250094Methyl (3β)-3-hydroxy-7-oxochol-5-en-24-oate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of finely ground K2CO3 (3.45 g, 25 mmoles) in 250 ml of methanol was added methyl 3β-acetoxy-7-oxochol-5-en-24-oate (1) (11.1 g, 25 mmoles). After stirring at 45° for 15 minutes in a N2 atmosphere, most of the methanol was removed in vacuo from the clear brown reaction mixture. The residue was suspended in H2O and extracted three times with CH2Cl2. The combined extracts were washed with H20 twice and saturated brine and dried with MgSO4. Evaporation in vacuo gave 10.1 g of nearly pure 2 as a pale yellow solid. The nuclear magnetic resonance data for this and subsequent Examples was taken at 400 MHz in CDCl3 : δ0.68 (s, 3H, 18-Me); 0.94 (d, 3H, 20-Me); 1.21 (s, 3H, 19-Me); 3.66 (s, 3H, CO2Me); 3.68 (m, 1H, 3-H); 5.70 (s, 1H, 6-H).

Workup

  1. customwas removed in vacuo from the clear brown reaction mixture
  2. extractionextracted three times with CH2Cl2
  3. washThe combined extracts were washed with H20 twice
  4. dry with materialsaturated brine and dried with MgSO4
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-46e939dce57c4b0899d3496b86eb41c3
Source dataset
uspto-grants-1997_01
Patent number
US05595996

Reaction notes

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