Pyridine → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester

HRID 20893

Reaction equation

HRID 20893 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH2:24][OH:25])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32]N=1)C.[C:36](Cl)(C1C=CC=CC=1)([C:45]1[CH:52]=[CH:51][C:48]([O:49][CH3:50])=[CH:47][CH:46]=1)[C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1.N1C=CC=C[CH:61]=1>>[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH:24]([C:32]1[CH:61]=[CH:30][CH:35]=[CH:34][CH:33]=1)[O:25][CH:36]([C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1)[C:45]1[CH:46]=[CH:47][C:48]([O:49][CH3:50])=[CH:51][CH:52]=1)=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 1049Pyridine2×HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 68638015[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

Product 1

HCID 131728206(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester

Procedure

Referring to scheme 1, compound 3a (14 g, 38.4 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (60 mL). To this solution dimethylamino pyridine (0.488 g, 4 mmol) and DMT-Cl (13.6 g, 40.3 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 4a (21.3 g, 83%) 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-b143499efae640acbbe3f9d0e652e296
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Linked notes

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