HCID 53885227, compound → HCID 53722959, compound

HRID 249888Notes

Reaction equation

HRID 249888 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])C1C=CC=CC=1.[H][H]>[Pd].CCOC(C)=O>[Si:16]([O:15][CH2:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][NH:8]1)([C:19]([CH3:22])([CH3:20])[CH3:21])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 53885227HCID 53885227, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53722959HCID 53722959, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (R)-4-benzyl-3-((tert-butyldimethylsilyloxy)methyl)morpholine (576 mg, 1.79 mmol) and 10% palladium on carbon in EtOAc (20 mL) was placed in a Parr shaker and hydrogenated at 45 psi hydrogen pressure for 48 h. The heterogeneous mixture was filtered through a pad of diatomaceous earth, washed with CH3OH (200 mL) and concentrated to provide (R)-3-((tert-butyldimethylsilyloxy)methyl)morpholine (414 mg, quant.) as a colorless oil. MS consistent.

Workup

  1. filtrationThe heterogeneous mixture was filtered through a pad of diatomaceous earth
  2. washwashed with CH3OH (200 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e65043ac8f2d4befa75d56baa5510a62
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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