Sodium t-butoxide → HCID 67515944, compound

HRID 1400050Notes

Reaction equation

HRID 1400050 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH2:27]([N:29]1[C:35](=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:28]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([N:32]4[CH2:33][CH2:34][C:35](=[O:36])[N:29]([CH2:27][CH3:28])[CH2:30][CH2:31]4)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 23676156Sodium t-butoxideHCID 534101084-Ethyl-1,4-diazepan-5-oneHCID 53432548tert-Butyl 1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate2×

Product 1

HCID 67515944HCID 67515944, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate I, 250 mg, 0.74 mmol) in anhydrous toluene (5 mL) were added Pd2(dba)3 (1.65 mg, 0.002 mmol), BINAP (3.42 mg, 0.006 mmol), sodium tert-butoxide (106.56 mg, 1.11 mmol) and 4-ethyl-[1,4]diazepan-5-one (210.2 mg, 1.48 mmol, prepared by the procedure as described in WO2008136754) at r.t. and reaction mixture was refluxed for 3 h. Reaction mixture was then concentrated and the crude product was purified by column chromatography (silica gel, 0.3:9.7 MeOH:CHCl3) to afford the title compound as viscous liquid (60 mg, 20.3%).

Workup

  1. customprepared by the procedure
  2. customat r.t.
  3. customreaction mixture
  4. temperaturewas refluxed for 3 h
  5. customReaction mixture
  6. concentrationwas then concentrated
  7. customthe crude product was purified by column chromatography (silica gel, 0.3:9.7 MeOH:CHCl3)

Sources & evidence

ORD record
ord-fdde982afe7646d88791881e175343a4
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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