2-Naphthol → HCID 12129393, compound

HRID 1281750Notes

Reaction equation

HRID 1281750 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 12129393HCID 12129393, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-naphthol (2.9 g) and 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (4 g) in tetrahydrofuran (30 ml) at 0° C. was added triphenylphosphine (5.2 g) and diethyl azodicarboxylate (3.2 ml). The reaction was allowed to warm to room temperature and stirred for 16 h. The solvent was removed in vacuo and the slurry taken up in EtOAc (30 ml) and washed with aqueous sodium hydroxide (1M, 2×30 ml), water (30 ml) and brine (30 ml). The organic extract was diluted with hexane (50 ml), and the precipitates were removed by filtration, and the filtrate dried over magnesium sulphate (1 g). The solvent was removed in vacuo to yield the title compound as a white solid (3.4 g).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with aqueous sodium hydroxide (1M, 2×30 ml), water (30 ml) and brine (30 ml)
  3. extractionThe organic extract
  4. additionwas diluted with hexane (50 ml)
  5. customthe precipitates were removed by filtration
  6. dry with materialthe filtrate dried over magnesium sulphate (1 g)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-72fde93a8e154ecf9f27c5284be954a0
Source dataset
uspto-grants-2002_09
Patent number
US06455531B1

Reaction notes

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