HCID 71279282, compound → HCID 71280487, compound

HRID 246762Notes

Reaction equation

HRID 246762 reaction equation
[N:1]([CH:4]1[CH2:9][O:8][CH2:7][CH:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5]1)=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:1][CH:4]1[CH2:9][O:8][CH2:7][CH:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:5]1

Participants

4

Reactant 1

HCID 71279282HCID 71279282, compound

Product 1

HCID 71280487HCID 71280487, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-azido-tetrahydro-2H-pyran-3-ylcarbamate (1 g, 4.13 mmol) in 30 mL of ethyl acetate was added Pd/C (10%, 1 g), the reaction mixture was stirred overnight at room temperature under a hydrogen filled balloon. The reaction mixture was filtered over celite, the filtrate was concentrated to give tert-butyl 5-amino-tetrahydro-2H-pyran-3-ylcarbamate (188 mg, 21%) as white solid. LCMS: (M+H)+=217; 1H NMR (300 MHz, CDCl3): δ 3.84-3.57 (m, 4H), 3.19-3.05 (m, 2H), 2.21-1.65 (m, 2H), 1.44 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e806a78433ab46049b4ce1157ec64960
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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