HCID 14003446, compound → HCID 14003453, compound

HRID 2118886Notes

Reaction equation

HRID 2118886 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:5]1=[O:25])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH:4]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]([CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:5]1=[O:25]

Participants

4

Reactant 1

HCID 14003446HCID 14003446, compound

Product 1

HCID 14003453HCID 14003453, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8.95 g of this azide in 75 ml ethanol is hydrogenated over 2 g 10% Pd-C at 45° C. for 5 hr. The solution is then filtered and concentrated to afford 8.3 g 3-amino-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one. NMR (CDCl3, TMS): δ1.4 (s, 9H); δ1.7-2.5 (M+s, 8H); δ3.4 (d, 1H, J=17 hz); δ3.95 (d, 1H, J=17 hz); δ4.0 (broad m, 1H); δ4.95 (broad d, 1H); δ7.3 (s, 5H).

Workup

  1. filtrationThe solution is then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-11eda285932f4d9a8fa8d713a8483640
Source dataset
uspto-grants-1987_07
Patent number
US04680392

Reaction notes

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