Chloroform → HCID 67067103, compound

HRID 605822Notes

Reaction equation

HRID 605822 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][CH:35]=1)[O:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:25])[CH2:20][CH2:19]1.[CH:36]1([CH2:42]O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)[Cl:64]>C1COCC1>[ClH:64].[CH:36]1([CH2:42][O:13][C:14]2[CH:15]=[C:16]([CH:33]=[CH:34][CH:35]=2)[O:17][CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:25])[CH2:22][CH2:23]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 5

HCID 6212ChloroformHCID 7507CyclohexanemethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67067094HCID 67067094, compound

Product 1

HCID 67067103HCID 67067103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.35 ml, 40% Tol solution) was dropwise added to a THF (5 ml) solution containing 3-pyridyl 4-(3-hydroxyphenoxy)-1-piperidinecarboxylate (160 mg), cyclohexylmethanol (87 mg) and triphenylphosphine (200 mg), at 0° C., followed by stirring at room temperature for 24 hours. The reaction solution was diluted with chloroform, washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:1 (v/v)). The resulting oil was dissolved in EtOAc (5 ml), 4 M hydrogen chloride/EtOAc solution (1 ml) was added thereto, followed by stirring at room temperature. The solvent was evaporated under reduced pressure, and the precipitated solid was washed with EtOAc/2-propanol and dried under reduced pressure to obtain 3-pyridyl 4-[3-(cyclohexylmethoxy)phenoxy]-1-piperidinecarboxylate hydrochloride (94 mg).

Workup

  1. customat 0° C.
  2. washwashed with aqueous saturated sodium hydrogencarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:1 (v/v))
  6. dissolutionThe resulting oil was dissolved in EtOAc (5 ml)
  7. addition4 M hydrogen chloride/EtOAc solution (1 ml) was added
  8. stirringby stirring at room temperature
  9. customThe solvent was evaporated under reduced pressure
  10. washthe precipitated solid was washed with EtOAc/2-propanol
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-fe495c45f9434bca9cd7624af4d91662
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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