HCID 86613242, compound → HCID 72457689, compound

HRID 1660706Notes

Reaction equation

HRID 1660706 reaction equation
[N:1]([CH:4]([CH3:23])[CH:5]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH:4]([CH3:23])[CH:5]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 86613242HCID 86613242, compound

Product 1

HCID 72457689HCID 72457689, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of azide 109 (35 mg, 0.10 mmol) in EtOH (1 mL), under argon, 10% Pd/c (7 mg) was added. The reaction was purged with H2 and stirred overnight under H2 atmosphere (1 atm). The mixture was filtered through Celite®. The filtrate was concentrated to yield the amine 110 (29 mg, 90%). The crude residue was used without further purification in the next step. 1H-NMR (500 MHz, CDCl3): 0.05 (s, 6H), 0.90 (s, 9H), 1.12 (d, J=6.7 Hz, 3H), 1.47 (s, 9H), 3.21-3.31 (m, 1H), 3.42-3.48 (m, 1H), 3.63-3.82 (m, 2H), 5.01-5.10 (m, 1H). 13C-NMR (125 MHz, CDCl3): −5.1, 19.1, 21.3, 26.2, 28.8, 47.1, 56.9, 64.5, 176.5.

Workup

  1. customThe reaction was purged with H2
  2. filtrationThe mixture was filtered through Celite®
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2b386e5ab67a468381d0bfc629898fff
Source dataset
uspto-grants-2011_10
Patent number
US08030279B2

Reaction notes

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