Trimethylamine → HCID 86584165, compound

HRID 2427815Notes

Reaction equation

HRID 2427815 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(NCCCO)(O[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH3:22][N:23]([CH3:25])C.P([O-])(O)(O)=[O:27].[K+]>C(Cl)Cl.CS(C)=O>[C:22](=[N:23][CH2:25][CH:1]([O:5][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:2]=[O:3])=[O:27]

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 65578Oxalyl chlorideHCID 516951Monobasic potassium phosphateHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 86584165HCID 86584165, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-48 °C

Procedure

335 mL of dimethylsulfoxide and 9 L of methylene chloride were combined and chilled to −48° C. 313 mL of oxalyl chloride was added over 25 minutes so that the temperature remained below −40° C. Cooled to −48° C. and added 500 grams of N-Cbz-3-amino-1-propanol dissolved in 1 L of methylene chloride so that the temperature remained below −40° C. Stirred for an additional hour at −45° C. 1325 mL of trimethylamine was added at such a rate that the temperature remained below −40° C. After stirring an additional 15 minutes at −40° C., the mixture was allowed to warm to −30° C., then added 2.5 L of 20% aqueous potassium dihydrogen phosphate. Stirred for one hour, then separated the layers, washed the organic layer with brine, and dried with magnesium sulfate. The resulting aldehyde was kept in solution at −20° C. until needed.

Workup

  1. customremained below −40° C
  2. temperatureCooled to −48° C.
  3. customremained below −40° C
  4. customremained below −40° C
  5. stirringAfter stirring an additional 15 minutes at −40° C.
  6. temperatureto warm to −30° C.
  7. stirringStirred for one hour
  8. customseparated the layers
  9. washwashed the organic layer with brine
  10. dry with materialdried with magnesium sulfate
  11. customwas kept in solution at −20° C.

Sources & evidence

ORD record
ord-d0be4bc7afb946488c0c5a5a56d1a96e
Source dataset
uspto-grants-2011_06
Patent number
US07968707B2

Reaction notes

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