HCID 66622747, compound → HCID 66622302, compound

HRID 409799Notes

Reaction equation

HRID 409799 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]([CH2:19][O:20][CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)[CH2:10][O:11]CC1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]([CH2:19][O:20][CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)[CH2:10][OH:11])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66622747HCID 66622747, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66622302HCID 66622302, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude [2-Benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-ethyl]-methyl-carbamic acid tert-butyl ester (1.25 g, 3.06 mmol) in MeOH (10 mL) was added Pd/C (300 mg). The mixture was transferred to an autoclave reactor, charged with 55 psi of hydrogen, and stirred. After 1.5 h, LCMS analysis indicated the completion of the reaction. The reaction mixture was then filtered through celite and concentrated under reduced pressure to give [1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-2-hydroxy-ethyl]-methyl-carbamic acid tert-butyl ester (0.875 g, 95%), which was used without purification. LRMS (M−Boc+H+) m/z 220.2.

Workup

  1. customThe mixture was transferred to an autoclave reactor
  2. customthe completion of the reaction
  3. filtrationThe reaction mixture was then filtered through celite and
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6925285c1db4478a418e6fb612d7ea3
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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