Morpholine → HCID 22789172, compound

HRID 1606351Notes

Reaction equation

HRID 1606351 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:31])[CH2:29]I)[CH2:20][C@@:19]2([CH3:32])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:33])[CH2:16][C@@:15]2([CH3:34])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(Cl)Cl>[OH:1][C@@H:2]1[C@@H:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:31])[CH2:29][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH2:20][C@@:19]2([CH3:32])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:33])[CH2:16][C@@:15]2([CH3:34])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22789171HCID 22789171, compound

Product 1

HCID 22789172HCID 22789172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3α-Hydroxy-2β-(4'-iodoacetoxy-n-butoxy)-5α-pregnane-11,20-dione (467 mg.) was dissolved in dried methylene chloride (30 ml.) and morpholine (1 ml.) added to this solution. The mixture was stirred at room temperature for 1 hour, a white precipitate forming in this time. The mixture was filtered and the filtrate evaporated to a yellow oil which was purified by preparative tlc in ethyl acetate (run twice) to give the title compound (220 mg.) as a colourless oil. [α]D + 57.1° (c 0.49).

Workup

  1. customa white precipitate forming in this time
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to a yellow oil which
  4. customwas purified by preparative tlc in ethyl acetate (run twice)

Sources & evidence

ORD record
ord-ad9bbeb31fc449338dfac135143e27c1
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

Loading…