HCID 12072786, compound → HCID 12072787, compound

HRID 1018672Notes

Reaction equation

HRID 1018672 reaction equation
[N:1]([C@H:4]1[CH2:10][CH2:9][CH2:8][O:7][C:6]2[CH:11]=[C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:13]([C:15]([NH2:17])=[O:16])=[CH:14][C:5]1=2)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][C@H:4]1[CH2:10][CH2:9][CH2:8][O:7][C:6]2[CH:11]=[C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:13]([C:15]([NH2:17])=[O:16])=[CH:14][C:5]1=2

Participants

4

Reactant 1

HCID 12072786HCID 12072786, compound

Product 1

HCID 12072787HCID 12072787, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-5-azido-8-cyclohexylmethoxy-2,3,4,5-tetrahydro-benzo[b]oxepine-7-carboxylic acid amide (2.5 g, 5.8 mmol) in EtOAc (20 mL) was added 10% Pd/C (0.25 g). The mixture was hydrogenated at STP for 17 h, filtered though glass, and concentrated to a white solid (1.8 g, 98%). MS [M−H]− 317, m.p. 145-146° C. Optical purity determined by Mosher Amide formation, 55% e.e.

Workup

  1. filtrationfiltered though glass
  2. concentrationconcentrated to a white solid (1.8 g, 98%)

Sources & evidence

ORD record
ord-f49c318f9e8649bc91bda57585865940
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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