Triphenylphosphine → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(dimethylamino)benzoate

HRID 644158Notes

Reaction equation

HRID 644158 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([N:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O[CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([O:1][C:2]2[CH:11]=[C:10]([N:12]([CH3:13])[CH3:14])[CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 21014871Methyl 4-(dimethylamino)-2-hydroxybenzoate

Product 1

HCID 57602452Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(dimethylamino)benzoateYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-hydroxy-4-(N,N-dimethylamino)benzoate (7.809 g, 40 mmol), 4-hydroxy-1-tert-butoxycarbonylpiperidine (8.048 g, 40 mmol), triphenylphosphine (11.02 g, 42 mmol), and THF (250 mL) at 0° C. was added diethyl azodicarboxylate (7.1 mL, 45.1 mmol), dropwise. The reaction was warmed to room temperature and stirred overnight. The reaction was concentrated, chromatographed (hexane to 30% EtOAc/hexane), and triturated with ether/hexane to give the desired product as a white solid (5.55 g, 37%).

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed (hexane to 30% EtOAc/hexane)
  3. customtriturated with ether/hexane

Sources & evidence

ORD record
ord-9546e7cffb144266bf3d1d03cfdccf61
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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