Ethyl Acetate → HCID 11058178, compound

HRID 2306233Notes

Reaction equation

HRID 2306233 reaction equation
[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][CH:25]2[N:28]=[N+]=[N-])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.[OH-].[Na+]>O>[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][CH:25]2[NH2:28])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10971697HCID 10971697, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11058178HCID 11058178, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 6-tert-butyldiphenylsilyloxy-1-indanyl azide, as described above in Step C, (6.10 g, 14.7 mmol) in TBF (150 mL) at 0° C. was added LiAlH4 (1.0 M in THF, 17.7 mL, 17.7 mmol), dropwise. The reaction mixture was stirred at 0° C. for 1 hour then EtOAc (0.7 mL) was added, followed by H2O (0.7 mL), then 15% aqueous NaOH (0.7 mL), then H2O (2.1 mL). The quenched mixture was stirred at ambient temperature for 18 hours, then filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CHCl3—1% MeOH—0.1% NH4OH, to yield the titled product.

Workup

  1. stirringThe quenched mixture was stirred at ambient temperature for 18 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with CHCl3—1% MeOH—0.1% NH4OH

Sources & evidence

ORD record
ord-aa73846674974ca6b60f4a1e9659312e
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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