3,5-Dichlorophenol → n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidine

HRID 2185479Notes

Reaction equation

HRID 2185479 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Cl:34][C:35]1[CH:36]=[C:37](O)[CH:38]=[C:39]([Cl:41])[CH:40]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][C:37]2[CH:36]=[C:35]([Cl:34])[CH:40]=[C:39]([Cl:41])[CH:38]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 115713,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22458487n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidineYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (786 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (603 mg), 3,5-dichlorophenol (489 mg) and diethyl azodicarboxylate (522 mg) in tetrahydrofuran (15 mL) at room temperature. After stirring at room temperature for 14 hr, the reaction mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6) to give the titled compound (815 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 1.75 (m, 2H), 1.90 (m, 2H), 3.37 (m, 2H), 3.66 (m, 2H), 4.44 (m, 1H), 6.80 (d, J=1.5 Hz, 2H), and 6.95 (s, 1H); mass spectrum (EI+) m/e 345 (M).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-64ab112964fc4ee797f7219fe2037cf1
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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