1,2-Dichloroethane → HCID 67263778, compound

HRID 1687067Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][C:12]2[CH:11]3[CH2:15][CH2:16][N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:17][C:18](C)=O.[BH4-].[Na+].Cl[CH2:24]CCl>C(O)(=O)C.C(Cl)Cl>[CH:16]([N:7]1[CH2:6][CH:12]2[CH2:11][CH2:10][CH:9]([C:17]3[CH:18]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][C:13]=32)[CH2:8]1)([CH3:15])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Nitro-1-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene (80 mg, 0.367 mmol) was placed in 1,2-dichloroethane (2 mL) and acetic acid (0.1 mL). Acetone (31.9 mg, 0.550 mmol, 40.4 μL, 1.5 eq) was added and the reaction was stirred for 5 minutes. Sodium borohydride (16.3 mg, 0.440 mmol, 1.2 eq) was added and the reaction was heated at 80° C. for 2 hours. The reaction was then diluted with CH2Cl2 (10 mL) and washed with water (10 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-15% MeOH/CH2Cl2 as the eluting solvent to obtain 10-isopropyl-4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene as pale orange oil (62 mg, 65%). LCMS (m/e) 261 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.02 (dd, 1H, J=2.2 and 8.1 Hz), 7.93 (d, 1H, J=2.2 Hz), 7.19 (d, 1H, J=8.1 Hz), 3.15-3.08 (m, 2H), 2.90-2.75 (m, 3H), 2.35 (t, 2H, J=9.5 Hz), 2.21 (d, 2H, J=8.8 Hz), 1.60-1.55 (m, 2H), 0.93 (d, 6H, J=6.6 Hz).

Workup

washwashed with water (10 mL)
dry with materialThe organic layer was dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-e9cb3632e1034f7fadd6417f946e37c3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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