HCID 131736940, compound → HCID 131736941, compound

HRID 56443Notes

Reaction equation

HRID 56443 reaction equation
[N:1]([C@@H:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][CH2:6][C@@H:5]1[NH:12][C:13](=[O:21])[O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][C@@H:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][CH2:6][C@@H:5]1[NH:12][C:13](=[O:21])[O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 131736940HCID 131736940, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 131736941HCID 131736941, compoundYield 118.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(trimethylsilyl)ethyl (3R,4R)-4-azido-6,6-dimethyl-tetrahydro-2H-pyran-3-ylcarbamate (1.3 g, 3.5 mmol) and 10% palladium on carbon (200 mg) in methanol (10 mL) was stirred at room temperature under 1 atm hydrogen atmosphere (hydrogen balloon) overnight. After that, the mixture was filtered through a pad of celite. The filtrate was concentrated to get the title compound (1.2 g, crude) as a yellow oil, which was used directly for the next step without further purification.

Workup

  1. filtrationAfter that, the mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-994c63f22ae74976b1cc59135d0b5865
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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