HCID 22220589, compound → HCID 69654744, compound

HRID 1794931Notes

Reaction equation

HRID 1794931 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1[C:34]2[NH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[C:25]([O:35][CH:36]2[O:38][C@H:37]2[CH3:39])=[CH:24][CH:23]=1>CO>[CH2:1]([N:8]([CH:9]1[CH2:10][N:11]([C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[CH2:12]1)[CH2:39][C@H:37]([OH:38])[CH2:36][O:35][C:25]1[C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:33][C:34]=2[CH:22]=[CH:23][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22220589HCID 22220589, compoundHCID 86584414HCID 86584414, compound

Product 1

HCID 69654744HCID 69654744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl-[1-(4-nitro-phenyl)-azetidin-3-yl]-amine (which was obtained in Example 398) (1.95 g, 6.87 mmol) and (2S)-3-(9H-carbazol-4-yloxy)-methyl oxirane (Berridge et al., Int. J. Radial. Appl. Instrum., 1992, 563) (1.64 g, 6.87 mmol) was stirred at reflux in anhydrous methanol for 24 hours. Methanol was removed in vacuo and the desired product was isolated using silica gel flash chromatography to give 3.01 g of product as a yellow solid; 1H NMR (300 MHz, CDCl3) δ2.90 (m, 2H), 3.04(s, 1H), 3.85 (m, 3H), 3.98(m, 3H), 4.23(m, 3H), 6.01(d, 2H, J=7.26 Hz), 6.61(d, 1H, J=8.10 Hz), 7.06(d, 1H, J=8.04 Hz), 7.17(t, 1H, J=2.14 Hz), 7.34(m, 7H), 7.97(d, 2H, J=9.12 Hz), 8.14(t, 2H, J=8.79 Hz); MS (ES) m/z: 522.9 (MH+); Anal. Calcd. for C31H30N4O4: C, 71.25; H, 5.79; N, 10.72. Found: C, 70.77; H, 6.17; N, 9.61.

Workup

  1. customMethanol was removed in vacuo

Sources & evidence

ORD record
ord-a0595e863e684e7c8abbc49cd5333066
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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