3-Hydroxybenzaldehyde → tert-Butyl 4-(3-formylphenoxy)piperidine-1-carboxylate

HRID 1985828Notes

Reaction equation

HRID 1985828 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[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(OC(C)C)=O)=O)(C)C.C1(C)C=CC=CC=1>O1CCCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 66880968DIAD toluene

Product 1

HCID 53439173tert-Butyl 4-(3-formylphenoxy)piperidine-1-carboxylateYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxybenzaldehyde (0.98 g), 1-t-butoxycarbonyl-4-hydroxypiperidine (2.41 g) and triphenylphosphine (3.15 g) were suspended in tetrahydrofuran (10 mL). To the mixture was added dropwise 40% azodicarboxylic acid diisopropyl ester-toluene solution (6.1 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/3) to give the title compound (0.74 g).

Workup

  1. temperaturecooling
  2. customThe solvent was removed under reduced pressure
  3. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-6254a4ce21f047c3b7e4164390af3a24
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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