Benzophenone imine → HCID 86607829, compound

HRID 1821999Notes

Reaction equation

HRID 1821999 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)[CH2:10][C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23](=[NH:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:36]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:16]=2)[CH2:10][C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 57893679HCID 57893679, compound

Product 1

HCID 86607829HCID 86607829, compound

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Heat a mixture of 4-(3-bromo-phenoxy)-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (preparation 23, 0.759 g), benzhydrylideneamine (0.446 g), racemic-2,2′-bis(diphenylphosphino)-1,1′ binaphthyl (50 mg) and sodium t-butoxide (0.269 g) in toluene (20 mL) at 100° C. After 10 min., add tris(dibenzylidineacetone)-dipalladium(0) (37 mg) and heat at 100° C. After 2.5 hr., partition between ethyl acetate-hexane (1:4) and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a 35 g silica gel column eluting with dichloromethane-2M NH3 in methanol gradient to give the crude title compound (0.74 g). Mass spectrum (electrospray) m/z 471 (M+1).

Workup

  1. temperatureHeat
  2. waitAfter 2.5 hr
  3. custom, partition between ethyl acetate-hexane (1:4) and saturated aqueous NaCl
  4. dry with materialdry over anhydrous sodium sulfate
  5. customevaporate
  6. custompurify on a 35 g silica gel column
  7. washeluting with dichloromethane-2M NH3 in methanol gradient

Sources & evidence

ORD record
ord-318ec1ae98de472291934a364695fe49
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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