3-Hydroxypyridine → methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate

HRID 465626Notes

Reaction equation

HRID 465626 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][OH:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=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>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][O:22][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10380582methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

Product 1

HCID 10000174methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate (1.61 g, 5.2 mmol) in methylene chloride (20 ml) is added 3-hydroxypyridine (0.51 g, 5.4 mmol) and triphenylphosphine (1.82 g, 7 mmol). The mixture is stirred at room temperature for 10 minutes and then diisopropyl azodicarboxylate (1.05 ml, 5.3 mmol) is added slowly. The mixture is allowed to stir for 2 hours and the solvent is evaporated. The residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent to obtain methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate; IR (CH2CL2): 1732, 1280, 1230, 1102 cm-1.

Workup

  1. stirringto stir for 2 hours
  2. customthe solvent is evaporated
  3. customThe residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-824fa8deaab54eebb44ab2d072a001b1
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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