Tetrahydrofuran → HCID 9906121, compound

HRID 375512Notes

Reaction equation

HRID 375512 reaction equation
[N:1]([C:4]1[C:21](=[O:22])[CH2:20][CH2:19][C@@:18]2([CH3:23])[C:5]=1[CH2:6][CH2:7][C@@H:8]1[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]1[CH2:10][CH2:11][C@@H:12]2[O:24][CH:25]1[CH2:27][CH2:26]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[NH2:1][C:4]1[C:21](=[O:22])[CH2:20][CH2:19][C@@:18]2([CH3:23])[C:5]=1[CH2:6][CH2:7][C@@H:8]1[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]1[CH2:10][CH2:11][C@@H:12]2[O:24][CH:25]1[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 15816457HCID 15816457, compound

Product 1

HCID 9906121HCID 9906121, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 4-azido-17β-(cyclopropyloxy)androst-4-en-3-one (1.32 q, 3.57 mM), triphenylphosphine (1.14 g, 4.97 mM), tetrahydrofuran (25 ml) and water (8 ml) was heated to reflux for 15 hours. The reaction was cooled and most of the solvent was evaporated. The residue was dissolved in dichloromethane, loaded onto a column of SiO2 and flash chromatographed (toluene--10% ethyl acetate) to give 4-amino-17β-(cyclopropyloxy)androst-4-en-3-one (0.53 g 43.1%), mp 85°-88° C. IR 3446, 3363, 1672, 1584 cm-1 ; MS (CI) m/z 344 (100%, M+ +1), 1H NMR (CDCl3), 0.38-0.61 (4H, m, 2×cyclopropyl (CH2 's), 0.74 (s, C18 -Me), 1.15 (s, C19 -Me), 3.25-3.33 (m, OCH), 3.44 (t+br s, C17 α-H+NH 2), 13C NMR (CDCl3), 88.95, 132.87, 138.90, 194.33. This compound has the following structure:

Workup

  1. temperatureto reflux for 15 hours
  2. temperatureThe reaction was cooled and most of the solvent
  3. customwas evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. customchromatographed (toluene--10% ethyl acetate)

Sources & evidence

ORD record
ord-6899882185d941bcbd9ac977a2490847
Source dataset
uspto-grants-1996_01
Patent number
US05486511

Reaction notes

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