2-Naphthol → HCID 22854931, compound

HRID 1901431Notes

Reaction equation

HRID 1901431 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C@H:4]1[CH2:8][C@H:7]([O:9][C:23]2[CH:22]=[CH:21][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 6884101-Benzyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 22854931HCID 22854931, compoundYield 212.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.0 g (53.7 mmol) of N-Cbz-cis-4-hydroxy-D-proline methyl ester, 11.3 g (78.4 mmol) of β-naphthol, and 20.5 g (78.2 mmol) of triphenylphosphine in 300 mL of THF was treated with 12.3 mL (78.1 mmol) of diethyl azidodicarboxylate over 0.5 hour. The reaction was stirred at room temperature for 18 hours and was quenched by the addition of 100 mL sat'd aq NaCl. The two layers were separated and the organic solution dried (Na2SO4). Evaporation of the solvent gave 46.2 g of an oil which was purified by flash chromatography (SiO2 ; gradient of 25 percent to 50 percent EtOAc in hexanes) to afford 15.2 g (37.5 mmol; 70 percent) of the title compound.

Workup

  1. customwas quenched by the addition of 100 mL
  2. customThe two layers were separated
  3. dry with materialthe organic solution dried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5a93d39a0e1a4ab5955e56c01c5620f9
Source dataset
uspto-grants-1996_11
Patent number
US05578574

Reaction notes

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