Pyridine → 4-Methyl-20-(10-undecenoyloxy)-5alpha-4-azapregnan-3-one

HRID 975845Notes

Reaction equation

HRID 975845 reaction equation
[OH:1][CH:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([N:12]([CH3:24])[C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3].N1C=CC=CC=1.[C:31](Cl)(=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41]>C(Cl)Cl>[CH3:24][N:12]1[C:13](=[O:23])[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@H:11]1[CH2:10][CH2:9][C@@H:8]1[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]1[CH2:6][CH2:5][C@@H:4]2[CH:2]([O:1][C:31](=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3804210-Undecenoyl chlorideHCID 2286256620-Hydroxy-4-methyl-5a-4-azapregnan-3-one

Product 1

HCID 228706344-Methyl-20-(10-undecenoyloxy)-5alpha-4-azapregnan-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20-hydroxy-4-methyl-5α-4-azapregnan-3-one (0.167 g, 0.5 mM) and pyridine (0.1 mL) in anhydrous methylene chloride (4.5 mL) at ice-bath temperatures was added 10-undecenoyl chloride (0.13 mL, 0.6 mM) dropwise. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stir overnight. After diluting further with methylene chloride the mixture was washed with dilute hydrochloric acid, water, and brine, and dried (Na2SO4). The residue obtained from concentration of the filtered solution was flash chromatographed on silica gel using ethyl acetate as eluant to give the title compound as a glaze. MS M+ calculated for C32H53NO3, mw=499.78; observed m/e 499.

Workup

  1. washwas washed with dilute hydrochloric acid, water, and brine
  2. dry with materialdried (Na2SO4)
  3. customThe residue obtained from concentration of the filtered solution
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-13ffd772ea8b47a4bc11fe96f0b584fc
Source dataset
uspto-grants-1997_03
Patent number
US05610162

Reaction notes

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