Sodium Methoxide → HCID 86622334, compound

HRID 501701Notes

Reaction equation

HRID 501701 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[CH:16][CH:17]=3)[C@H:12]2[N:22]=[N+:23]=[N-:24])=O)=CC=1)([O-])=O.C[O-].[Na+]>CO.C(Cl)Cl>[N:22]([C@@H:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:20][CH3:21])[CH:14]=2)[CH2:19][C@@H:11]1[OH:10])=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 86622332HCID 86622332, compound

Product 1

HCID 86622334HCID 86622334, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Step AC (4): To a solution of (1R,2S)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoate (248 mg) from Step AC (3) in methanol (2.8 mL) and DCM (2.4 mL) was added sodium methoxide (114 mg), and the reaction mixture was stirred at rt for 30 min. the solvents were removed in vacuo, and water was added. The aqueous layer was separated, and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo, and the residue was purified by preparative TLC eluting with 30% EtOAc/70% hexanes to give (1R,2S)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol compound as a white solid (100 mg). 1H NMR (400 MHz, CDCl3) δ 7.15 (1H, d), 6.91 (1H, d), 6.87 (1H, dd), 4.72 (1H, d), 4.57 (1H, t), 3.80 (3H, s), 3.09 (1H, dd), and 2.84 (1H, dd). The ee of this product was 86% by chiral HPLC (chircel OJ-H column, 4.6×250 mm, 5 μm; mobile phase: 5% ethanol in CO2; flow rate: 2.0 mL/min). Retention time of the title compound: 10.04 min; Retention time of the other enantiomer: 7.38 min.

Workup

  1. customwere removed in vacuo, and water
  2. additionwas added
  3. customThe aqueous layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. customthe residue was purified by preparative TLC
  10. washeluting with 30% EtOAc/70% hexanes

Sources & evidence

ORD record
ord-d94fb790ff534372a5e2199e71568f7e
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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