Chloroform → HCID 67067103, compound

HRID 2074270Notes

Reaction equation

HRID 2074270 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-cd8f54b163f74eaf8263ece01335acbc
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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