Acetonitrile → HCID 86614564, compound

HRID 1672383Notes

Reaction equation

HRID 1672383 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:9][C:10]1([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.F[Si-2](F)(F)(F)(F)F.[H+].[H+]>O>[CH2:1]([N:8]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:9][C:10]1([CH2:13][OH:14])[CH2:11][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 86614565HCID 86614565, compound

Product 1

HCID 86614564HCID 86614564, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of methyl (benzyl{[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopropyl]methyl}amino)acetate (4.0 g, 0.010 mol) in ACN (100 mL, 2 mol) was added at RT, fluorosilicic acid in water (2.00 M, 10.6 mL). The resulting mixture was stirred at RT overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3 until the reaction mixture was alkaline and then extracted with EtOAc (2×). The organic extracts were combined and washed with brine, then dried (MgSO4), filtered and concentrated in vacuo to afford the desired product (1.1 g), which was identified by 1H NMR spectroscopy and used in the next step without further purification.

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 until the reaction mixture
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7792702c8fad416a9e69caa60e9bd521
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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