Triacetoxyperiodinane → [(R)-2-(3'-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester

HRID 70910Notes

Reaction equation

HRID 70910 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([CH2:23][OH:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([CH:23]=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67208767HCID 67208767, compound

Product 1

HCID 86648198[(R)-2-(3'-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl esterYield 52.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, to a solution of [(R)-2-(3′-chloro-biphenyl-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (2.0 g, 5.53 mmol) in DCM (30 mL) is added Dess-Martin periodinane (2.81 g, 6.63 mmol). After being stirred at room temperature for 2 h, the reaction mixture is diluted with EtOAc and washed with saturated NaHCO3 aqueous solution and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography (silica gel, eluent; heptane/EtOAc=100:0 to 0:100) to give [(R)-2-(3′-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester (1.05 g). HPLC retention time=1.27 minutes (condition A): MS (m+1)=360.

Workup

  1. washwashed with saturated NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography (silica gel, eluent; heptane/EtOAc=100:0 to 0:100)

Sources & evidence

ORD record
ord-b4e998f893e649b0a936e5588e57accb
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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