Potassium Carbonate → tert-Butyl 3-(benzyloxy)-1-(hydroxymethyl)propylcarbamate

HRID 14078Notes

Reaction equation

HRID 14078 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]([C:20](OC)=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:20][OH:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 54564501methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

Product 1

HCID 21087273tert-Butyl 3-(benzyloxy)-1-(hydroxymethyl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cold solution of methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate (6 g, 18.6 mmol) in absolute ethanol (100 mL) is added sodium borohydride (2.8 g, 74.2 mmol), and the reaction is refluxed 2 h. The solution is cooled, excess saturated potassium carbonate added, and stirred 16 h at room temperature. The ethanol is removed under reduced pressure, and the aqueous solution is extracted with chloroform. The organic layer is washed with saturated sodium bicarbonate, saturated sodium sulfate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 296.2 [M+H]+.

Workup

  1. temperaturethe reaction is refluxed 2 h
  2. temperatureThe solution is cooled
  3. customThe ethanol is removed under reduced pressure
  4. extractionthe aqueous solution is extracted with chloroform
  5. washThe organic layer is washed with saturated sodium bicarbonate, saturated sodium sulfate
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4c9f3efc1264bc88a48d53a053d8398
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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