Sodium Bicarbonate → tert-butyl N-methyl-N-(3-oxopropyl)carbamate

HRID 453890Notes

Reaction equation

HRID 453890 reaction equation
CC1(C)N([O])C(C)(C)CCC1.[OH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])O.[Na+].[O-]Cl.[Na+]>ClCCl.O.CCOC(C)=O.CCCCCC>[CH3:24][N:16]([CH2:15][CH2:14][CH:13]=[O:12])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724126TempoHCID 10375241tert-Butyl (3-hydroxypropyl)methylcarbamateHCID 23665760Sodium Hypochlorite

Product 1

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

A catalytic amount of TEMPO was added to a mixture of 20 g (1 eq.) tert-butyl 3-hydroxypropyl(methyl)carbamate in 200 ml dichloromethane and 17.7 g (2 eq.) sodium hydrogen carbonate in 100 ml water at 0° C. 140 ml (7 eq.) NaOCl were then added dropwise over a period of 30 min to the solution at a temperature of 0° C. and the reaction mixture obtained was stirred for a further 15 min at 0° C. The reaction course was monitored by thin-layer chromatography (40% EtOAc/hexane). Once the conversion was complete, the reaction mixture was mixed with 150 ml water and the phases were separated. The organic phase was dried over Na2SO4. Following removal of the solvent under reduced pressure, 16 g (85%) of product were obtained in the form of a yellowish oil.

Workup

  1. customthe reaction mixture obtained
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-adebfa8a4ef84668935490f8a29074b3
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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