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Pyridine → 17beta-(1-Oxo-3-methylbutyl)-6-azaandrost-4-en-3-one

HRID 1077595
Notes
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Reaction equation

HRID 1077595 reaction equation
[C:1]([C@H:4]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:5]12[CH2:6]C(O)=O)[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH2:19][CH2:20]1)[N:15](C(C)(C)C)[CH2:14]3)(O)=[O:2].N1C=CC=CC=1.S(Cl)(Cl)=O.[CH2:41]([Mg]Br)[CH:42]([CH3:44])[CH3:43]>C1(C)C=CC=CC=1.CN(C)C=O>[O:2]=[C:1]([C@H:4]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:5]12[CH3:6])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH2:19][CH2:20]1)[NH:15][CH2:14]3)[CH2:41][CH:42]([CH3:44])[CH3:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 8674903417beta-Carboxy-6-t-butylcarboxy-6-azaandrost-4-en-3-oneHCID 178418816HCID 178418816, compound

Product 1

HCID 1006692717beta-(1-Oxo-3-methylbutyl)-6-azaandrost-4-en-3-one

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Alternatively, a solution of 17β-carboxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one (260 mg, 0.62 mmol), example 3, Part F, is dissolved in toluene (10 mL) and treated with pyridine (3 eq) and catalytic dimethylformamide, cooled to 0° C., and thionyl chloride added (80 μL, 1.10 mmol). The reaction is then allowed to warm to room temperature and is stirred for 1 hr. The solids are then removed by filtration, the solution concentrated, the resulting crude acid chloride dissolved in THF (6 mL), CuL added (120 mg, 0.62 mmol), cooled to -78° C. and treated with isobutylmagnesium bromide (2.0M in diethyl ether, 0.5 mL, 1 mmol). The reaction is allowed to warm to room temperature, stirred for 30 min and is worked up as in Part C above to give 17β-(1-oxo-3-methylbutyl)-6-azaandrost-4-en-3-one.

Workup

  1. temperatureto warm to room temperature
  2. customThe solids are then removed by filtration
  3. concentrationthe solution concentrated
  4. dissolutionthe resulting crude acid chloride dissolved in THF (6 mL)
  5. additionCuL added (120 mg, 0.62 mmol)
  6. temperaturecooled to -78° C.
  7. temperatureto warm to room temperature
  8. stirringstirred for 30 min

Sources & evidence

ORD record
ord-c09b852582a342669d6e1f5208b9bc31
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05543406

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes