Potassium trimethylsilanolate → HCID 59367580, compound

HRID 2079826Notes

Reaction equation

HRID 2079826 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH:13]1[CH:18]2[CH:14]1[CH2:15][N:16]([C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=1)[CH2:17]2.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH:13]1[CH:14]2[CH:18]1[CH2:17][N:16]([C:19]1[CH:29]=[CH:28][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[CH2:15]2

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolate2×HCID 59367585HCID 59367585, compound

Product 1

HCID 59367580HCID 59367580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-{6-[(naphthalen-2-ylmethyl)-amino]-3-aza-bicyclo[3.1.0]hex-3-yl}-benzoate (500 mg, 1.29 mmol) was stirred in THF (30 ml) with potassium trimethylsilanolate (332 mg, 2.58 mmol) at r.t. under N2 for 6 h. More potassium trimethylsilanolate (332 mg, 2.58 mmol) was added and the reaction stirred at 50° C. for 4 days. The reaction was allowed to cool to r.t. and a precipitate formed. This was isolated by filtration, dried and used in the next step without further purification. LCMS purity 60%, m/z 359 [M+H]+.

Workup

  1. temperatureto cool to r.t.
  2. customa precipitate formed
  3. customThis was isolated by filtration
  4. customdried
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-970981c1ec55410ebb27b2b136a9ce0d
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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