Triacetoxyperiodinane → Benzyl N-methyl-N-(2-oxoethyl)carbamate

HRID 2364438Notes

Reaction equation

HRID 2364438 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:15])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:15][N:4]([CH2:3][CH:2]=[O:1])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 13279869N-Cbz-N-methyl-2-aminoethanol

Product 1

HCID 12010768Benzyl N-methyl-N-(2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of phenylmethyl (2-hydroxyethyl)methylcarbamate (2.02 g, 9.64 mmol) and Dess Martin's Reagent (6.36 g, 15.6 mmol) in CH2Cl2 (100 mL) were combined under nitrogen and stirred for 4 h at ambient temperature. Added CH2Cl2 (100 mL) and washed the organics with 2M Na2CO3 (aq.), saturated NaHCO3, water, and brine, dried over Na2SO4, filtered and evaporated in vacuo. Purified the residue by flash chromatography using silica gel and a gradient between 0 and 10% MeOH in CH2Cl2 over 20 minutes to provide the desired material, after combining and concentrating pure fractions in vacuo, as a yellow viscous oil: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.03 (d, J=6.59 Hz, 3 H), 4.06 (s, 1 H), 4.13 (s, 1 H), 5.12-5.21 (m, 2 H), 7.29-7.40 (m, 5 H), 9.63 (d, J=16.28 Hz, 1 H); ES+ MS: 230 (M+Na+).

Workup

  1. washAdded CH2Cl2 (100 mL) and washed the organics with 2M Na2CO3 (aq.), saturated NaHCO3, water, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurified the residue by flash chromatography

Sources & evidence

ORD record
ord-1f459239381f44f296c24f5c23926ca2
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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