HCID 21709010, compound → 5-(Tert-butyloxycarbonyl)-7-hydroxy-1-(hydroxymethyl)-1,2,3,4-tetrahydro-5h-naphtho[1,2-b]azepine

HRID 651875Notes

Reaction equation

HRID 651875 reaction equation
C([O:8][C:9]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:12]2[N:13]([CH2:25][O:26]S(C)(=O)=O)[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]=2[CH:10]=1)C1C=CC=CC=1>[Pd]>[C:21]([O:20][C:18]([CH:17]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:25][OH:26])[C:12]2[C:31]3[C:36]([C:9]([OH:8])=[CH:10][C:11]1=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 1

HCID 21709010HCID 21709010, compound

Product 1

HCID 217089835-(Tert-butyloxycarbonyl)-7-hydroxy-1-(hydroxymethyl)-1,2,3,4-tetrahydro-5h-naphtho[1,2-b]azepine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the general procedure detailed for 86, 84 (0.015 g, 0.035 mmol, 1 equiv) was treated with 10% Pd—C (0.001 g, 0.3 equiv) followed by aqueous HCO2NH4 (0.2 mL, 25% w/v, 23 equiv). Filtration and concentration gave 101 as an analytically pure colorless oil in quantitative yield (0.012 g, 0.012 g theoretical) which crystallized upon storage: mp 202-203° C.; 1H NMR 400 MHz, CDCl3) major rotamer δ 9.19 (s, 1H), 8.07-8.05 (m, 1H), 7.26-7.22 (m, 1H), 6.81-6.75 (m, 2H), 6.50 (s, 1H), 4.28-4.24 (m, 1H), 4.18-4.08 (m, 2H), 3.89-3.86 (m, 1H), 2.85-2.79 (m, 1H), 2.11-2.07 (m, 1H), 1.94-1.91 (m, 1H), 1.70-1.67 (m, 2H), 1.62 (s, 9H); 1H NMR 400 MHz, acetone-d6) major rotamer 9.03 (s, 1H), 8.26 (d, J=8.2 Hz, 1H), 8.07 (d, J=8.6 Hz, 1H), 7.55-7.51 (m, 1H), 7.46-7.43 (m, 1H), 6.74 (s, 1H), 4.37-4.33 (m, 1H), 4.03-3.99 (m, 1H), 3.91-3.80 (m, 1H), 3.61-3.52 (m, 2H), 2.73-2.66 (m, 1H), 2.36-2.32 (m, 1H), 2.20-2.10 (m, 1H), 1.60-1.55 (m, 1H), 1.33 (s, 9H); IR (film) νmax 3272, 2976, 2925, 1662, 1621, 1596 cm−1; FABHRMS (NBA-NaI) m/z 344.1855 (M+H+, C20H25NO4 requires 344.1862).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d7e9fefef0c5413395a8663492679daa
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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