Nitrogen → HCID 66821254, compound

HRID 1044745Notes

Reaction equation

HRID 1044745 reaction equation
N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[BH4-].[Na+].O>CO>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][OH:17])=[CH:14][N:15]=1)[CH3:10])([CH3:4])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 86649487HCID 86649487, compound

Product 1

HCID 66821254HCID 66821254, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazole-5-carbaldehyde (457 mg, 1.79 mmol) was dissolved in MeOH (8 mL). NaBH4 (92 mg, 2.33 mmol) was added portionwise at 0° C. and the reaction mixture stirred at rt for 20 min. Water (16 mL) was added and the MeOH removed under reduced pressure. The mixture was then extracted with EA (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The title compound was obtained as a colorless oil. LC-MS-conditions 02: tR=0.97 min; [M+H]+=258.37.

Workup

  1. customthe MeOH removed under reduced pressure
  2. extractionThe mixture was then extracted with EA (2×20 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-f164011fc3cc48c0a9627c3df01a1f34
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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