1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → 1-Tritylpiperidine

HRID 1171736Notes

Reaction equation

HRID 1171736 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=S)C.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>CN(C)C=O>[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine2×HCID 22253565HCID 22253565, compoundHCID 178418634HCID 178418634, compound2×

Product 1

HCID 153723441-TritylpiperidineYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-({1-[3-ethoxycarbonyl]propyl]-1H-tetrazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (715.6 mg) in N,N-dimethylformamide (10 ml) were added thioacetic acid (950 μl) and N,N-dimethylformamide dineopentyl acetal (3.7 ml). The resulting mixture was stirred at room temperature for one hour. Then, thioacetic acid (950 μl) and N,N-dimethylformamide dineopentyl acetal (3.7 ml) were added further, and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The organic layer partitioned was washed with water and saturated aqueous sodium chloride successively, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (1:9 to 3:7) as the eluent to afford crude (E)-4-(acetylsulfanyl)-3-({1-[3-ethoxycarbonyl]propyl]-1H-tetrazol-5-yl}methylidene)-1-(triphenylmethyl)piperidine (419 mg) as a yellow oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customThe organic layer partitioned
  4. washwas washed with water and saturated aqueous sodium chloride successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on silica gel using
  8. additiona mixture of ethyl acetate and hexane (1:9 to 3:7) as the eluent

Sources & evidence

ORD record
ord-3e4bbd26817f4875a72c73e0ab67b2f6
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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