1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl Ester

HRID 1893025

Reaction equation

HRID 1893025 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH:20]([OH:22])[CH2:19][CH:18]1[CH2:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](Cl)(C1C=CC=CC=1)([C:35]1[CH:42]=[CH:41][C:38]([O:39][CH3:40])=[CH:37][CH:36]=1)[C:27]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[CH:29][CH:28]=1>N1C=CC=CC=1.CN(C1C=CC=CN=1)C>[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH:20]([OH:22])[CH2:19][CH:18]1[CH:23]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:24][CH:26]([C:27]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[CH:29][CH:28]=1)[C:35]1[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[CH:41][CH:42]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 72260745[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-hexyl]-carbamic Acid Benzyl Ester

Product 1

HCID 131728214(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl EsterYield 436.1%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 1049PyridineSolvent2×

Procedure

Compound 29 (6 g, 17 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (60 mL). To this solution dimethylamino pyridine (0.207 g, 1.7 mmol) and DMT-Cl (6 g, 17.9 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. The excess DMT-Cl was quenched by the addition of methanol (25 mL). The solution was dried under reduced pressure. To the residue was suspended in ethyl acetate (300 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. 24.2 g of the crude product was obtained after removal of the solvent. Upon purification over silica gel using 2% MeOH/DCM compound 30 (8.7 g, 79%) was obtained as white foamy solid.

Workup

  1. customThe excess DMT-Cl was quenched by the addition of methanol (25 mL)
  2. customThe solution was dried under reduced pressure
  3. washwashed with saturated bicarbonate solution, brine and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-eac3cb325da5411ca91d6451a765e47c
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Linked notes

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