Sodium Hydroxide → HCID 86651896, compound

HRID 1183026Notes

Reaction equation

HRID 1183026 reaction equation
NC([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)C#N.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:25].[OH-].[Na+]>C(Cl)Cl>[CH3:21][C:18]1([CH3:22])[O:17][C@H:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH:5]=[O:25])=[CH:9][CH:10]=2)[CH2:20][O:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66917020HCID 66917020, compound2×

Product 1

HCID 86651896HCID 86651896, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-[4-((R)-2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-phenyl]-propan-1-ol (Intermediate B, Step 2) (1.18 g, 4.42 mmol) in DCM (150 mL) is added Dess-Martin periodinane (1.88 g, 4.42 mmol). The reaction mixture is stirred at RT for 3 h then treated with 1 N NaOH solution (50 mL) and stirred at RT for 1 h. The organic layer is separated, dried (MgSO4), filtered and concentrated in vacuo to give a clear oil. Purification by flash column chromatography (SiO2, EtOAc:iso-hexane, gradient 17-25%) affords the title compound. [M+H]+ 265.

Workup

  1. stirringstirred at RT for 1 h
  2. customThe organic layer is separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a clear oil
  7. customPurification by flash column chromatography (SiO2, EtOAc:iso-hexane, gradient 17-25%)

Sources & evidence

ORD record
ord-c022294b51c345d3a87228d43409a81c
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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