Monobenzone → Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate

HRID 1091984Notes

Reaction equation

HRID 1091984 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]2)=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7638MonobenzoneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22458519Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylateYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropyl azodicarboxylate (2.36 mL) was added to a solution of 4-(benzyloxy)phenol (2.0 g), tert-butyl 4 hydroxypiperidine-1-carboxylate (2.41 g) and triphenylphosphine (3.67 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 20% ethyl acetate in hexane to give tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate as a light orange oil (3.25 g); NMR Spectrum: (CDCl3) 1.47 (s, 9H), 1.65-1.77 (m, 2H), 1.83-1.93 (m, 2H), 3.24-3.34 (m, 2H), 3.65-3.76 (m, 2H), 4.27-4.35 (m, 1H), 5.01 (s, 2H), 6.80-6.93 (m, 4H), 7.28-7.45 (m, 5H); Mass Spectrum: (M-tBuOCO)+H+ 284.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThis resulting mixture was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-143f55191e2343a7ba921008d2b5dfe2
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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