HCID 66622747, compound → HCID 66622302, compound

HRID 340937Notes

Reaction equation

HRID 340937 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-cd336df3c1184ca48e51bc6b44b738fe
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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