tert-Butyl carbamate → 154748-66-0

HRID 1050943Notes

Reaction equation

HRID 1050943 reaction equation
[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)[O:22][C:20](=O)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15]C1=2)=O>C(Cl)Cl>[O:22]=[CH:20][CH2:19][CH:18]1[CH2:15][CH:16]([NH:7][C:6](=[O:8])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:17]1

Participants

4

Reactant 2

HCID 77922tert-Butyl carbamateHCID 159087Triacetoxyperiodinane

Product 1

HCID 86175322154748-66-0Yield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-hydroxy-ethyl)-cyclobutyl]-carbamic acid tert-butyl ester (5.2 g, 24.1 mmol) in anhydrous DCM (100 mL) was added Dess-Martin periodinane (20.5 g, 48.3 mmol) and stirred at room temperature for 5 hrs. The mixture was quenched with Na2S2O3 solution, extracted with DCM. The organic phase was concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (eluted with PE:EA=5:1) to give the title compound (2.7 g, yield 52%) as an oily liquid.

Workup

  1. customThe mixture was quenched with Na2S2O3 solution
  2. extractionextracted with DCM
  3. concentrationThe organic phase was concentrated under reduced pressure
  4. customto give a residue, which
  5. customwas purified by column chromatography on silica gel (eluted with PE:EA=5:1)

Sources & evidence

ORD record
ord-0f823ab0faf347848bf0ac0860ae61fb
Source dataset
uspto-grants-2016_07
Patent number
US09388141B2

Reaction notes

Loading…