HCID 67104984, compound → HCID 67105767, compound

HRID 1173592Notes

Reaction equation

HRID 1173592 reaction equation
[Si:1]([O:8][CH:9]([C:27]1([C:30]([O:32]CC)=O)[CH2:29][CH2:28]1)[CH:10]([N:12](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[OH-].[Pd+2].[OH-].[C]>[Si:1]([O:8][CH:9]1[C:27]2([CH2:29][CH2:28]2)[C:30](=[O:32])[NH:12][CH:10]1[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67104984HCID 67104984, compound

Product 1

HCID 67105767HCID 67105767, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-[(1RS,2RS)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)propyl]cyclopropanecarboxylate (1.36 g) in methanol (16 mL) was added 10% palladium hydroxide-carbon (containing 50% water, 280 mg), and the mixture was stirred at room temperature for 18 hr under a hydrogen atmosphere. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/4) to give the title compound as a colorless solid (yield: 164 mg, yield:22.8%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/4)

Sources & evidence

ORD record
ord-63bee1948bfa4a9cbecc06ebbb9c36e8
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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