tert-Butyl (2,3-dihydroxypropyl)methylcarbamate → tert-butyl N-methyl-N-(2-oxoethyl)carbamate

HRID 1354525Notes

Reaction equation

HRID 1354525 reaction equation
[C:1]([N:8]([CH3:14])[CH2:9][CH:10]([OH:13])CO)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O>[C:1]([N:8]([CH3:14])[CH2:9][CH:10]=[O:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 1

HCID 17878865tert-Butyl (2,3-dihydroxypropyl)methylcarbamate

Product 1

HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-Boc-N-methyl-1-amino-2,3-propandiol (20g, 0.097 mol) in water (100 ml) was added KIO4 (24.68g, 0.108 mol). The reaction mixture was stirred for 2.5 hr under an atmosphere of nitrogen and then filtered. The filtrate was extracted with chloroform (5×50 ml). The resulting chloroform extracts are dried over MgSO4, filtered, and evaporated to dryness. The title compound 13.26g (79%) was isolated as a clear oil (bp 76-80° C. at 0.5 mm Hg).

Workup

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with chloroform (5×50 ml)
  3. dry with materialThe resulting chloroform extracts are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-bdb416062209445ab264f217412f1bea
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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