HCID 58188283, compound → HCID 58188371, compound

HRID 1845133Notes

Reaction equation

HRID 1845133 reaction equation
[N:1]([C@@H:4]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[N:18][CH:19]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-]>[Pd].C(OCC)(=O)C>[Si:7]([O:6][CH2:5][C@H:4]([C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][CH:15]=1)[NH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9]

Participants

4

Reactant 1

HCID 58188283HCID 58188283, compound

Product 1

HCID 58188371HCID 58188371, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-5-(1-azido-2-(tert-butyldimethylsilyloxy)ethyl)-2-methylpyridine (11.21 g, 0.036 mol), ethyl acetate (400 mL), and 10% Pd—C (7 g) was stirred under H2 (1 atm) for 1 hour. The catalyst was filtered off and the filtrate was concentrated to get the title product as an oil. 1H NMR (CD3OD, 400 MHz): 8.39 (d, 1H, J=2.0 Hz), 7.74 (dd, 1H, J=8.0, 2.4 Hz), 7.28 (d, J=8.0 Hz, 1H), 3.98 (t, 1H, J=6.0 Hz), 3.73 (d, 2H, J=6.0 Hz), 2.51 (s, 3H), 0.86 (s, 9H), −0.02 (s, 6H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cfb96f6f4b10463fae8fc206eb849b46
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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