4-Benzylphenol → (S)-2-[(4-Benzylphenoxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 750016Notes

Reaction equation

HRID 750016 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][OH:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]2[CH:25]=[CH:26][C:27](O)=[CH:28][CH:29]=2)=[CH:21][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C:20]2[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=2)=[CH:29][CH:28]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 75634-BenzylphenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1514243(S)-1-N-Boc-piperidine-2-ethanol

Product 1

HCID 68998783(S)-2-[(4-Benzylphenoxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)—N-Boc-piperidine-2-ethanol (1.00 g, 4.36 mmol), 4-hydroxydiphenylmethane (0.884 g, 4.79 mmol), and triphenylphosphine (1.26 g, 4.80 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added diisopropyl azodicarboxylate (0.92 ml, 4.80 mmol), and the resulting mixture was stirred at ambient temperature for about 20 h. The clear, yellow solution was concentrated in vacuo. The crude liquid was purified by silica gel flash chromatography to obtain the title compound as a clear, yellow oil (1.20 g, 70%): 1H NMR (400 MHz; CDCl3) δ 7.35 (m, 2H), 7.17 (m, 3H), 7.07 (d, 2H, J=8.8 Hz), 6.79 (d, 2H, J=8.8 Hz), 4.46 (m, 1H), 3.97 (m, 5H), 2.80 (br t, 1H, J=13.2 Hz), 2.12 (m, 1H), 1.85 (m, 1H), 1.60 (m, 5H), 1.40 (m, 10H). MS, m/z 418 (M+Na)+.

Workup

  1. concentrationThe clear, yellow solution was concentrated in vacuo
  2. customThe crude liquid was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c739ca3b1f7149d491a20d86dd768ca7
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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