Triacetoxyperiodinane → tert-butyl N-methyl-N-(3-oxopropyl)carbamate

HRID 1480413Notes

Reaction equation

HRID 1480413 reaction equation
[C:1]([O:5][C:6](=[O:13])[N:7]([CH2:9][CH2:10][CH2:11][OH:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:8][N:7]([CH2:9][CH2:10][CH:11]=[O:12])[C:6](=[O:13])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 10375241tert-Butyl (3-hydroxypropyl)methylcarbamate

Product 1

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available tert-butyl(3-hydroxypropyl)(methyl)carbamate (1.858 g, 9.82 mmol) was solubilised in DCM (40 ml) and treated with sodium bicarbonate (4.12 g, 49.1 mmol) followed by Dess-Martin reagent (5.21 g, 12.28 mmol). The reaction mixture was stirred at RT for 2 hrs and then partitioned between DCM and sodium bicarbonate solution. Sodium thiosulphate was added and the organic portion was separated. The aqueous layer was extracted with DCM (×2) and the combined organic extracts were dried over MgSO4 (anh), filtered and evaporated under reduced pressure to afford the title compound without further purification;

Workup

  1. custompartitioned between DCM and sodium bicarbonate solution
  2. additionSodium thiosulphate was added
  3. customthe organic portion was separated
  4. extractionThe aqueous layer was extracted with DCM (×2)
  5. dry with materialthe combined organic extracts were dried over MgSO4 (anh)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-13354f6343704e7d94169a1aa35d7910
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

Loading…