3-(Dimethylamino)-1,2-propanediol → 1-(4,4'-Dimethoxytrityloxy)-3-dimethylamino-2-propanol

HRID 1988501Notes

Reaction equation

HRID 1988501 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH:4]([OH:7])[CH2:5][OH:6].[CH3:9][O:10][C:11]1[CH:32]=[CH:31][C:14]([C:15](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([O:6][CH2:5][CH:4]([OH:7])[CH2:3][N:2]([CH3:8])[CH3:1])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:14]2[CH:31]=[CH:32][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 790783-(Dimethylamino)-1,2-propanediolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)3×

Product 1

HCID 597532281-(4,4'-Dimethoxytrityloxy)-3-dimethylamino-2-propanolYield 105.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Dimethylamino-1,2-propanediol (6.0 g, 50 mmol) was weighed into a 1 L round bottomed flask with a stir bar. The flask was sealed, flushed with argon, charged with pyridine and cooled to 0° C. 4,4′-Dimethoxytrityl chloride (17.9 g, 1.05 equiv.) was weighed into a 100 mL round bottomed flask, sealed and then dissolved in pyridine (80 mL). The 4,4′-dimethoxytrityl chloride solution was transferred to the stirring reaction mixture slowly, using additional fresh pyridine (20 mL) to effect the transfer of residual 4,4′-dimethoxytrityl chloride. The reaction was allowed to come to room temperature while stirring overnight. The reaction was concentrated in vacuo and re-dissolved in dichloromethane (300 mL). The organic phase was washed with saturated bicarbonate (2×200 mL) and brine (1×200 mL), dried over MgSO4, filtered, concentrated and dried under high vacuum to afford 22.19 g of a yellow gum that was used without further purification.

Workup

  1. customThe flask was sealed
  2. customflushed with argon
  3. additioncharged with pyridine
  4. customsealed
  5. customto come to room temperature
  6. concentrationThe reaction was concentrated in vacuo
  7. dissolutionre-dissolved in dichloromethane (300 mL)
  8. washThe organic phase was washed with saturated bicarbonate (2×200 mL) and brine (1×200 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-c1984557ff7442449f0ab413b2683a20
Source dataset
uspto-grants-2010_01
Patent number
US07641915B2

Reaction notes

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