Water → HCID 86734024, compound

HRID 1576776Notes

Reaction equation

HRID 1576776 reaction equation
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[CH3:26][C@H:27]1[O:32][C@H:31]([CH3:33])[CH2:30][NH:29][CH2:28]1.O>O1CCCC1>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][N:29]2[CH2:28][C@H:27]([CH3:26])[O:32][C@@H:31]([CH3:33])[CH2:30]2)[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11137133trans-2,6-DimethylmorpholineHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 86734024HCID 86734024, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21-Bromo-3α-hydroxy-5α-pregnane-11,20-dione (1 g.) was dissolved in dry tetrahydrofuran (50 ml.) and cis/trans-2,6-dimethylmorpholine (1 ml.) added to the solution. The mixture was refluxed for 4 hours. The mixture was poured into water, the emulsion extracted into ether, and the combined extracts washed with water, dried over anhydrous sodium sulphate and evaporated to a pale yellow foam (1.07 g.) which was purified by preparative T.L.C. in ethyl acetate. The faster running band (Rf ~0.6) gave 3α-hydroxy-21-(trans-2',6'-dimethylmorpholino)-5α-pregnane-11,20-dione (150 mg., 14%) as a white foam. [α]D + 70.5° (c 0.42).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. extractionthe emulsion extracted into ether
  3. washthe combined extracts washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to a pale yellow foam (1.07 g.) which
  6. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-4a66d6682b5941fe95409286f16b977d
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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