4-Hydroxybenzaldehyde → tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylate

HRID 1636843Notes

Reaction equation

HRID 1636843 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20](O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22632605tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylateYield 150.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.9 g (0.040 mol) 4-hydroxy-benzaldehyde, 10.0 g (0.050 mol) 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (analogously to K. L. Bhat, D. M. Flanagan, M. M. Jouille, Synth. Commun. 1985, 15, 587-598) and 13.1 g (0.050 mol) triphenylphosphine in 200 ml tetrahydrofuran is mixed at 5° C. with 7.9 ml (0.050 mol) azodicarboxylic acid diethyl ester and stirred for 24 hours at room temperature. After concentration the residue is purified by chromatography on a silica gel column (mobile solvent: isohexane/ethyl acetate 8:2, 7:3). After concentrating the appropriate column fractions one obtains 18.4 g (85%) of the title compound as a yellowish solid substance. Melting point. 63-64° C.; EI-MS: 305 (M+).

Workup

  1. concentrationAfter concentration the residue
  2. customis purified by chromatography on a silica gel column (mobile solvent: isohexane/ethyl acetate 8:2, 7:3)
  3. concentrationAfter concentrating the appropriate column fractions one

Sources & evidence

ORD record
ord-422732bc6153488ca312ef137bc313ae
Source dataset
uspto-grants-2000_03
Patent number
US06037334

Reaction notes

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