Triphenylphosphine → n-Tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidine

HRID 2185484Notes

Reaction equation

HRID 2185484 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:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=1O.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:36]2[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:35]=2[Cl:34])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 120082-Chloro-5-methylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22458419n-Tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidineYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (786 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (603 mg), 2-chloro-5-methylphenol (428 mg) and diethyl azodicarboxylate (522 mg) in tetrahydrofuran (10 mL) at room temperature. After stirring at room temperature for 18 hr, the reaction mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6, v/v) to give the titled compound (489 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.84 (m, 4H), 2.28 (s, 3H), 3.44 (m, 2H), 3.65 (ddd, J=4.0, 8.0, 12.7 Hz, 2H), 4.49 (m, 1H), 6.69 (d, J=8.0 Hz, 1H), 6.75 (s, 1H), and 7.19 (d, J=8.0 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-de6af0a4d35849e7b81b749235b136df
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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