HCID 67287398, compound → HCID 67286790, compound

HRID 74987Notes

Reaction equation

HRID 74987 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15]C)[CH:10]1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])C1C=CC=CC=1>C(OCC)(=O)C.[H][H].[Pd]>[OH:15][CH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([O:8][CH3:1])[CH:10]1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 1

HCID 67287398HCID 67287398, compound2×

Product 1

HCID 67286790HCID 67286790, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A solution of racemic [1-benzyloxy-3-methoxy-2-cyclohexanoxy]tert-butyl-dimethylsilane, 51e, (3.4 g, 9.7 mmol) was dissolved in ethyl acetate (50 mL) and hydrogenated under 45 PSI of hydrogen with Pd—C 10% for 1 h. The reaction mixture was filtered over a nylon/fiberglass filter to provide, after concentration in vacuo 2.72 g of desired product 51f. This material was used directly in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over a nylon/fiberglass
  2. filtrationfilter
  3. customto provide
  4. concentrationafter concentration in vacuo 2.72 g of desired product 51f
  5. customThis material was used directly in the next step without further purification

Sources & evidence

ORD record
ord-489be99e263b4e139b2aeccfa5109086
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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