HCID 11394714, compound → HCID 11267935, compound

HRID 431743Notes

Reaction equation

HRID 431743 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:8]=1[N+:25]([O-])=O)(=[O:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:8]=1[NH2:25])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 11394714HCID 11394714, compound

Product 1

HCID 11267935HCID 11267935, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[4-(N-t-butoxycarbonylamino)-2-nitronaphthalen-1-yl]ethyl acetate (1.0 g, 2.67 mmol) in THF (40 mL) was added to a suspension of 10% Pd—C (0.1 g) in chilled THF (10 mL) and the suspension was hydrogenated (with shaking) at 55 psi at room temperature for 1 h. The suspension was filtered over Celite and the filtrate was concentrated under reduced pressure to afford 2-[2-amino-4-(N-t-butoxycarbonylamino)naphthalen-1-yl]ethyl acetate as an orange foam. The compound was washed with diisopropyl ether to afford as a pale yellow solid (0.48 g, 52%).: mp 138-140° C.; 1H NMR (CDCl3, 500 MHz) δ 7.86 (d, 9.0, 1H), 7.72 (d, 8.5, 1H), 7.56 (brs, 1H), 7.46 (t, 7.0, 1H), 7.27 (m, 1H), 6.85 (brs, 1H), 4.26 (t, 8.0, 2H), 4.22 (brs, 2H), 3.24 (t, 7.5, 2H), 2.10 (s, 3H), 1.56 (s, 9H); FABMS (NBA) m/z 344 (M+), IR (neat) νmax 3379, 2977, 1727, 1626, 1534, 1504, 1456, 1391, 1367, 1238, 1158, 1043, 894, 758, 730 cm−1.

Workup

  1. filtrationThe suspension was filtered over Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff1ef33f451a4134b99a5249af8b6cb9
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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