1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86707461, compound

HRID 338938Notes

Reaction equation

HRID 338938 reaction equation
[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:1][C@@H:2]2[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 13329885tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

Product 1

HCID 86707461HCID 86707461, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (2.79 g, 13.7 mmol) in anhydrous pyridine (144 mL) was added 4,4′-(chloro(phenyl)methylene)bis(methoxybenzene) (5.43 g 15.2 mmol) and the resulting mixture stirred at ambient temperature for 4 days. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure. The residue was stirred in diethyl ether (150 mL) and the solid which precipitated was collected by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane) to afford (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (4.48 g, 65%).

Workup

  1. customThe reaction was quenched with methanol (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. stirringThe residue was stirred in diethyl ether (150 mL)
  4. customthe solid which precipitated
  5. filtrationwas collected by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane)

Sources & evidence

ORD record
ord-37b5001076fa4bceb9a55543c9b63e49
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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