Cyclopropylamine → HCID 9797517, compound

HRID 840174Notes

Reaction equation

HRID 840174 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[NH:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=O.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.[BH4-].[Na+]>C(Cl)(Cl)Cl.C(O)C.CCOC(C)=O>[CH:22]1([NH:25][C@H:3]2[CH2:4][CH2:5][C@H:6]3[C@H:7]4[C@H:17]([CH2:18][CH2:19][C@:2]23[CH3:1])[C@:15]2([CH3:16])[C:10]([NH:11][C:12](=[O:20])[CH2:13][CH2:14]2)=[CH:9][CH2:8]4)[CH2:24][CH2:23]1

Participants

7

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 11403477[4aR-(4aα,4bβ,6aα,9aβ,9bα)]-3,4,4a,4b,5,6,6a,8,9,9a,9b,10-Dodecahydro-4a,6a-dimethyl-1H-indeno[5,4-f]quinoline-2,7-dione

Product 1

HCID 9797517HCID 9797517, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Aza-androst-5(6)-ene-3,17-dione (0.53 g, 1.844 mmol) dissolved in chloroform (CHCl3, 10.0 mL) and cyclopropylamine ((CH2)2CHNH2, ALDRICH, 4.12 g, 72.15 mmol) is added, and the reaction mixture is heated to reflux under nitrogen. After 15 hours, the reaction is cooled to room temperature and analysis indicates the stoichiometric conversion to the cyclopropylimine. Sodium borohydride (NaBH4, ALPHA, 0.3574 g, 0.4475 mmol) in ethanol (21 mL) is added and the reaction is stirred at room temperature under nitrogen. After 21 hours, the reaction is worked-up by diluting with EtOAc (50 mL), washing in water (2×40 mL), in brine (40 mL) and drying over MgSO4, filtering and evaporating the solvent to obtain the crude product of the title compound. The crude product is further purified by flash chromatography (10.5″, 5.25 g, SiO2; elute first with 25% EtOAc/×25% CH2Cl2/50% hexane then with 15% iPrOH/×85%×CH2Cl2) to give 17β-cyclopropylamino-4-aza-androst-5(6)-en-3-one in excellent purity (0.4948 g, 1.5063 mmol). Yield: 82%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux under nitrogen
  3. waitAfter 21 hours
  4. washwashing in water (2×40 mL), in brine (40 mL)
  5. dry with materialdrying over MgSO4
  6. filtrationfiltering
  7. customevaporating the solvent

Sources & evidence

ORD record
ord-8cff86e3c2764422bb8d053d7e9e5f0c
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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