Sodium Carbonate → 4-Amino-3-(boc-amino)-tetrahydro-2H-pyran

HRID 39435Notes

Reaction equation

HRID 39435 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[C:13](=O)[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH:13]([NH2:22])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 20780854tert-Butyl (4-oxotetrahydro-2H-pyran-3-yl)carbamate

Product 1

HCID 673586134-Amino-3-(boc-amino)-tetrahydro-2H-pyranYield 44.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (CAS 477584-38-6, 446 mg, 2.07 mmol) was dissolved in 20 mL methanol. Ammonium acetate (1.63 g, 21 mmol) and sodium cyanoborohydride (507 mg, 8.1 mmol) were added and the reaction mixture was stirred at room temperature for 2 days. Ethyl acetate and 2N sodium carbonate solution were added. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified with flash column chromatography on silica eluting with a gradient (dichloromethane/methanol/ammonia 100:0:0→140:10:1) to provide 199 mg (44%) of the title compound as a white solid. MS (m/e): 161.2 (M-butene)+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with flash column chromatography on silica eluting with a gradient (dichloromethane/methanol/ammonia 100:0:0→140:10:1)

Sources & evidence

ORD record
ord-133cdeae23114177a1bb8afb1d8ca630
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

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