Sodium Thiosulfate → tert-butyl N-methyl-N-(2-oxoethyl)carbamate

HRID 590393Notes

Reaction equation

HRID 590393 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:12][N:4]([CH2:3][CH:2]=[O:1])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateYield 124.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300 mg, 1.71 mmol)) in dry CH2Cl2 (8.5 mL) under argon was added portion wise Dess-Martin periodinane (762 mg, 1.8 mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3 h. The mixture was poured into saturated solutions of NaHCO3 (50 mL) and Na2S2O3 (50 mL) and more CH2Cl2 (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHCO3 (1×20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98%) as colourless oil together with a yellow solid, which was used in the next step without further purification.

Workup

  1. additionthe addition
  2. stirringIt was well-stirred at room temperature for 30 minutes
  3. customThe organic phase was separated
  4. washwashed with sat. aq. NaHCO3 (1×20 mL)
  5. dry with materialIt was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac7d1cd108004339a9812450bd6d536b
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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