Tetrahydrofuran → HCID 12796519, compound

HRID 2049481Notes

Reaction equation

HRID 2049481 reaction equation
[CH3:1][N:2]([C@@H:4]1[CH2:21][C@@]2(C)[C@@H:15]([CH2:16]C=C2)[C@H:14]2[C@H:5]1[C@:6]1([CH3:26])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:22])[C@@H:8]([O:23][CH2:24][CH3:25])[CH2:7]1)[CH3:3].[Br:27]N1C(=O)CCC1=O.Cl(O)(=O)(=O)=O.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>O>[Br:27][C@@H:43]1[C@@H:44]([OH:40])[CH2:16][C@H:15]2[C@H:14]3[C@H:5]([C@H:4]([N:2]([CH3:3])[CH3:1])[CH2:21][C@:42]12[CH3:41])[C@:6]1([CH3:26])[C@H:11]([CH2:10][C@H:9]([OH:22])[C@@H:8]([O:23][CH2:24][CH3:25])[CH2:7]1)[CH2:12][CH2:13]3

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 67184N-bromobutanimideHCID 70583955HCID 70583955, compound

Product 1

HCID 12796519HCID 12796519, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11α-N,N-dimethylamino-2β-ethoxy-5α-androst-16-en-3α-ol (1.6 g) in tetrahydrofuran (40 ml) and water (16.5 ml) containing N-bromosuccinimide (1.05 g) and 60% perchloric acid (2 ml) was kept overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and potassium carbonate solution and the organic extract was washed, dried (Na2SO4) and evaporated in vacuo. Purification of the residue by preparative thin layer chromatography over silica (ethyl acetate:petroleum ether 1:1) and crystallization from ether afforded the title compound m.p. 173°-174°, [α]D -53.6°.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and potassium carbonate solution
  2. extractionthe organic extract
  3. washwas washed
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customPurification of the residue by preparative thin layer chromatography
  7. customover silica (ethyl acetate:petroleum ether 1:1) and crystallization from ether

Sources & evidence

ORD record
ord-0da5de52765d491e87fcbc48362623dc
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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