Triphenylphosphine → HCID 17755962, compound

HRID 491600Notes

Reaction equation

HRID 491600 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[C:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25]O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][O:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 692642-Chloro-5-nitrophenolHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 17755962HCID 17755962, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-5-nitro phenol (10 g, 63.497 mmol), N-boc-4-piperidine methanol (13.67 g, 63.49 mmol), and PPh3 (16.63 g, 63.49 mmol) in 130 mL THF, cooled at −20° C. was added dropwise over 1.5 h a 50 mL THF solution containing DIAD (12.75 ml, 64.76 mmol). The mixture turned a deep red. The reaction was warmed gradually to RT and stirred for 18 h. The mixture was concentrated in vacuo, dissolved in Et2O, washed once with water, then NaHCO3 (sat). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was treated with a mixture of hexanes and EtOAc (1:1) and the solid was filtered. The filtrate was evaporated and the residue was purified by silica gel column chromatography to yield the title compound as a yellow solid. MS (MH+)=NA; Calc'd 370.13 for C17H23ClN2O5.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in Et2O
  3. washwashed once with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with a mixture of hexanes and EtOAc (1:1)
  8. filtrationthe solid was filtered
  9. customThe filtrate was evaporated
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c9673f858bba46509945e5e70e6a597e
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

Loading…