HCID 131726837, compound → HCID 131726838, compound

HRID 901997Notes

Reaction equation

HRID 901997 reaction equation
[N:1]([C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 131726837HCID 131726837, compound

Product 1

HCID 131726838HCID 131726838, compoundYield 106.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of trans 3-azido-2-carbo-t-butoxymethoxy-1,2,3,4-tetrahydronaphthalene (750 mg, 2.47 mmol) in methanol (10 mL) at room temperature was added 20% palladium on carbon (60 mg). The resulting mixture was stirred under a hydrogen balloon. After 16 h, the reaction mixture was filtered through a plug of Celite® and the filtrate was concentrated under vacuum to obtain the title compound (730 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.04-7.17 (m, 4H), 4.25 (d, J=16.7 Hz, 1H), 4.11 (d, J=16.7 Hz, 1H), 4.68 (m, 1H), 3.32-3.47 (m, 2H), 3.25 (dd, J=6.7, 16.5 Hz, 1H), 3.02 (m, 1H), 2.85 (dd, J=10.7, 16.5 Hz, 1H), 1.49 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered through a plug of Celite®
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a09816ad2eed46c08c723a57dfb86428
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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