Triphenylphosphine → HCID 86624650, compound

HRID 1091980Notes

Reaction equation

HRID 1091980 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]([F:28])([O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[CH:17]([F:19])[F:18].[OH:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:15][C:16]([F:28])([O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:23][CH:22]=1)[CH:17]([F:18])[F:19].[F:15][C:16]([F:28])([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH:30]2[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]2)=[CH:25][CH:26]=1)[CH:17]([F:18])[F:19]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27786294-(1,1,2,2-tetrafluoroethoxy)phenol

Product 2

HCID 44469961HCID 44469961, compoundHCID 86624650HCID 86624650, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]piperidine was prepared as follows: Diisopropyl azodicarboxylate (2.25 mL) was added to a solution of 4-(1,1,2,2-tetrafluoroethoxy)phenol (2.0 g), tert-butyl 4 hydroxypiperidine-1-carboxylate (2.3 g) and triphenylphosphine (3.5 g) in dichloromethane (30 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 the tert-butyl 4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]piperidine-1-carboxylate as a light green oil (3.3 g); NMR Spectrum: (DMSOd6) 1.39 (s, 9H), 1.43-1.57 (m, 2H), 1.82-1.95 (m, 2H), 3.09-3.24 (m, 2H), 3.56-3.70 (m, 2H), 4.47-4.59 (m, 1H), 6.73 (tt, 1H), 7.03 (d, 2H), 7.16 (d, 2H).

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-3572991e11eb49ea8be3fed4dd06f00a
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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