Triphenylphosphine → HCID 72299154, compound

HRID 2191102Notes

Reaction equation

HRID 2191102 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[N:41][CH:42]=1.[CH2:44]([N:51]1[CH2:56][CH2:55][CH:54]([CH2:57]O)[CH:53]([C:59]2[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=2)[CH2:52]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[CH2:44]([N:51]1[CH2:56][CH2:55][CH:54]([CH2:57][O:43][C:40]2[CH:39]=[CH:38][C:37]([Cl:36])=[CH:42][N:41]=2)[CH:53]([C:59]2[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=2)[CH2:52]1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 72299169HCID 72299169, compoundHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 72299154HCID 72299154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

In a 100 mL four necked round bottom flask with a magnetic stirrer and inert atmosphere 1.3 g polymer bound triphenylphosphine was stirred in 15 mL THF. At 0-5° C. a solution of 514 mg (2.23 mmol) di-tert-butyl azodicarboxylate in 8 mL THF and a solution of 271 mg (2.1 mmol) 5-chloro-2-hydroxypyridine in 10 mL THF was added. The mixture was stirred for 20 min at 0° C.-5° C. 441 mg (1.4 mmol) [(3RS, 4RS)-1-benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-methanol in 8 mL THF was added. The ice bath was removed and the brownish mixture was stirred for 2 h at room temperature. The mixture was filtrated over decalite and washed with ethyl acetate. The solvents were evaporated and the residue purified by column chromatography on silica gel eluting with ethyl acetate/toluene to yield after evaporation of the product containing fractions 0.3 g (50%) of the title compounds as white solid. MS (m/e): 298.3/427.1 [(M+H)+].

Workup

  1. customThe ice bath was removed
  2. stirringthe brownish mixture was stirred for 2 h at room temperature
  3. filtrationThe mixture was filtrated over decalite
  4. washwashed with ethyl acetate
  5. customThe solvents were evaporated
  6. customthe residue purified by column chromatography on silica gel eluting with ethyl acetate/toluene
  7. customto yield
  8. customafter evaporation of the product
  9. additioncontaining fractions 0.3 g (50%) of the title compounds as white solid

Sources & evidence

ORD record
ord-7cdbf5a106704ed5ad603ff44dfed3fd
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

Loading…