Hydrochloric Acid → HCID 66955253, compound

HRID 1948532Notes

Reaction equation

HRID 1948532 reaction equation
C([C:3]1([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1)#N.Cl.[C:22](=[O:25])([O-])[O-:23].[Cs+].[Cs+].[Si](Cl)(C)(C)[CH3:29]>CO>[CH3:18][Si:17]([CH3:19])([CH3:20])[O:16][C:3]1([C:22]([O:23][CH3:29])=[O:25])[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 10796Cesium carbonateHCID 58374194Tert-butyl 3-cyano-3-(trimethylsilyloxy)piperidine-1-carboxylate

Product 1

HCID 66955253HCID 66955253, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 3-cyano-3-(trimethylsilyloxy)piperidine-1-carboxylate, Preparation 34A (170 mg, 0.570 mmol) was treated with 6N HCl in MeOH (10 mL) at 80° C. for 12 hours. Solvents were removed in vacuo and the resulting material was dissolved in MeOH (10 mL). HCl (g) was bubbled through the mixture for 15 minutes. The solids were concentrated in vacuo. The residue was dissolved in DCM (10.00 mL) and cesium carbonate (928 mg, 2.85 mmol) was added. Next, TMS—Cl (0.146 mL, 1.139 mmol) was added and the mixture was stirred for 1 hour. The mixture was filtered and the solids were concentrated in vacuo and taken to the next step without further purification.

Workup

  1. customSolvents were removed in vacuo
  2. dissolutionthe resulting material was dissolved in MeOH (10 mL)
  3. customHCl (g) was bubbled through the mixture for 15 minutes
  4. concentrationThe solids were concentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM (10.00 mL)
  6. filtrationThe mixture was filtered
  7. concentrationthe solids were concentrated in vacuo
  8. customtaken to the next step without further purification

Sources & evidence

ORD record
ord-5e18151ba7b7423fb6a52dcf8095f488
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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