1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 54152206, compound

HRID 1740474Notes

Reaction equation

HRID 1740474 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([C:22](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[CH2:14][O:15][C:22]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:39][CH:38]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 10680283tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 54152206HCID 54152206, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2R,4R)-1-(tert-Butyloxycarbonyl)-2-hydroxymethyl-4-hydroxypyrrolidine 37 (4.4 g, 20.28 mmol) was dissolved in dry pyridine (50 ml) and allowed to stir under argon atmosphere. To this stirred solution was added TEA (2.53 g, 25 mmol) followed by 4,4'-dimethoxytrityl chloride (7.45 g, 22 mmol). The reaction mixture was stirred at room temperature for 12 h and quenched with MeOH (10 ml). The solution was evaporated to dryness and dissolved in EtOAc (200 ml). The EtOAc layer was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine. The organic extract was dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The required fractions were pooled together and evaporated to give 8.09 g (100%) of an orange foam. 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 3.74 (s, 6H, 2.OCH3), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 6.82 (d, 4H, Ph), and 7.26-8.00 (m, 9H, Ph).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 h
  2. customquenched with MeOH (10 ml)
  3. customThe solution was evaporated to dryness
  4. dissolutiondissolved in EtOAc (200 ml)
  5. washThe EtOAc layer was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography over silica gel
  10. customevaporated

Sources & evidence

ORD record
ord-f6f221a7097d46afb7755768d5624c9a
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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