1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 86609431, compound

HRID 1171682Notes

Reaction equation

HRID 1171682 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[N:10]=[N:9][C:8](/[CH:11]=[C:12]2\[CH2:13][N:14]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:16][CH:17]\2O)=[N:7]1)=[O:4].[C:38]([OH:41])(=[S:40])[CH3:39].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>ClCCl.O.C1(C)C=CC=CC=1>[C:38]([S:40][CH:17]1[CH2:16][CH2:15][N:14]([C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:13]/[C:12]/1=[CH:11]\[C:8]1[N:9]=[N:10][N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:7]=1)(=[O:41])[CH3:39]

Participants

7

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138777HCID 23138777, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609431HCID 86609431, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of (E)-3-{[2-(methoxycarbonylmethyl)-2H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (1.5 g) in a mixed solvent of dichloromethane (30 ml) and toluene (30 ml) was added thioacetic acid (2.2 ml) and N,N-dimethylformamide dineopentyl acetal (8.5 ml). After the mixture was stirred at 50° C. for 2 hours, it was cooled, water and dichloromethane were added and the layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using hexane, ethyl acetate, and dichloromethane (2:1:1) as an eluent to afford (E)-4-(acetylsulfanyl)-3-{[2-(methoxycarbonylmethyl)-2H-tetrazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (containing impurity, gross amount: 880 mg, gross yield: 58.4%).

Workup

  1. temperatureit was cooled
  2. customthe layers were separated
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe extract was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-210680327bc9401198731d91b1d9d720
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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