Sodium Hydroxide → HCID 67305374, compound

HRID 61423Notes

Reaction equation

HRID 61423 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:16][CH:15]([OH:17])[CH2:14][CH2:13][CH:12]1[C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21]1)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([CH:11]1[CH2:16][C:15](=[O:17])[CH2:14][CH2:13][CH:12]1[C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:21]1)=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 673050735-Hydroxy-2-(3-phenyl-pyrrolidine-1-carbonyl)-cyclohexanecarboxylic Acid Benzyl Ester

Product 1

HCID 67305374HCID 67305374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol compound from Step 2 (400 mg) was added Dess-Martin reagent (500 mg) and the mixture was stirred at rt for 3 h. After the reaction was complete the mixture was diluted with methylene chloride followed by the addition of 0.1 N NaOH aqueous solution (12 mL) and the stirring was continued for about 20 min. The organic phases were washed with 0.1 N NaOH solution, brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatographed (eluting with 5% methanol in methylene chloride). MS (ESI): 406.1 (M+H+)

Workup

  1. waitthe stirring was continued for about 20 min
  2. washThe organic phases were washed with 0.1 N NaOH solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash
  6. customchromatographed
  7. wash(eluting with 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-b83ead8d820b4bceb2da183fa61882ba
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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