Sodium hydride → HCID 131726837, compound

HRID 901996Notes

Reaction equation

HRID 901996 reaction equation
[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[OH:14])=[N+:2]=[N-:3].[H-].[Na+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>O1CCCC1>[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[O:14][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15637840HCID 15637840, compound

Product 1

HCID 131726837HCID 131726837, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trans 3-azido-2-hydroxy-1,2,3,4-tetrahydronaphthalene (95 mg, 0.55 mmol) in tetrahydrofuran (5 mL) at 0° C. under nitrogen was added sodium hydride (60% oil dispersion, 26 mg, 0.66 mmol). Gas evolution was observed and the reaction mixture turned cloudy. After slowly warming up to room temperature for 20 min, t-butyl bromoacetate (0.12 mL, 0.83 mmol) was added. After 2 h, the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution and diluted with ethyl acetate. The organic layer was washed with aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (7% ethyl acetate in hexane was used) to obtain the title compound (90 mg). 13C NMR (400 MHz, CDCl3) δ 169.59, 133.18, 132.59, 128.88, 128.45, 126.50, 126.37, 81.76, 78.89, 67.99, 61.40, 33.95, 33.51, 28.08. 1H NMR (400 MHz, CDCl3) δ 7.03-7.17 (m, 4H), 4.20 (s, 2H), 3.91 (m, 1H), 3.73 (m, 1H), 3.29 (dd, J=5.7, 16.8 Hz, 1H), 3.16 (dd, J=5.7, 16.8 Hz, 1H), 2.90 (dd, J=8.4, 17.0 Hz, 1H), 2.80 (dd, J=8.4, 17.0 Hz, 1H), 1.48 (s, 9H).

Workup

  1. customthe reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with aqueous ammonium chloride solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography (7% ethyl acetate in hexane was used)

Sources & evidence

ORD record
ord-9bf3c0c9bba34f13996f813bab4a174c
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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