Triphenylphosphine → Tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate

HRID 1091986Notes

Reaction equation

HRID 1091986 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:16]1[CH:35]=[CH:34][CH:33]=[CH:32][C:17]=1[O:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.[F:36][C:37]([F:42])([F:41])[CH2:38][CH2:39][OH:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:36][C:37]([F:42])([F:41])[CH2:38][CH2:39][O:40][C:34]1[CH:35]=[CH:16][C:17]([O:18][CH:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:23][CH2:24]2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1375123,3,3-Trifluoro-1-propanolHCID 66592967HCID 66592967, compound

Product 1

HCID 66592935Tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylateYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropyl azodicarboxylate (0.97 mL) was added to a solution of tert-butyl 4-(hydroxyphenoxy)piperidine-1-carboxylate (1.2 g), 3,3,3-trifluoro-1-propanol (0.56 g) and triphenylphosphine (1.5 g) in dichloromethane (15 mL). The reaction mixture was stirred at ambient temperature for 18 hours and then concentrated at reduced pressure. This resulting mixture was purified by silica column chromatography, eluting with a gradient of 0 to 15% ethyl acetate in hexane to give tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate as a white solid (0.6 g); NMR Spectrum: (CDCl3) 1.47 (s, 9H), 1.66-1.77 (m, 2H), 1.83-1.94 (m, 2H), 2.52-2.66 (m, 2H), 3.24-3.34 (m, 2H), 3.65-3.75 (m, 2H), 4.11 (t, 2H), 4.27-4.37 (m, 1H), 6.78-6.89 (m, 4H); Mass Spectrum: M+H+ 390 and (M-tBuOCO)+H+ 290.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThis resulting mixture was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cf9d9f3fecbc42b8a82ae4c6bc93ebc1
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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