Sodium borohydride → HCID 49806571, compound

HRID 2381212Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:25])([CH3:24])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([C:9]3=[CH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[O:26][CH3:27])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:24])([CH3:25])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([CH:9]3[CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[O:26][CH3:27])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (600 mg, 1.64 mmol) in methanol (50 mL) was added sodium borohydride (65 mg, 1.7 mmol) in small portions at 0° C. After stirring at 0° C. for 2 h, the mixture was concentrated in vacuo. The resulting residue was extracted with diethyl ether (2×50 mL), washed with water (2×25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 9,10-dimethoxy-8,8-dimethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (0.5 g, 83%). LC/MS m/e calcd for C22H25NO4 (M+H)+: 368.45, observed: 368.1; 1H NMR (400 MHz, MeOD) δ ppm 1.51 (s, 3 H) 1.72 (s, 3 H) 2.63-2.84 (m, 3 H) 2.84-2.93 (m, 1 H) 3.06 (dd, J=16.17, 3.79 Hz, 1 H) 3.21-3.28 (m, 1 H) 3.83 (s, 3 H) 3.86 (s, 3 H) 4.09 (dd, J=11.37, 3.54 Hz, 1 H) 5.88 (s, 2 H) 6.58 (s, 1 H) 6.75 (s, 1 H) 6.80-6.85 (m, 1 H) 6.86-6.91 (m, 1 H).

Workup

concentrationthe mixture was concentrated in vacuo
extractionThe resulting residue was extracted with diethyl ether (2×50 mL)
washwashed with water (2×25 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fee61bcd512a482b80884a2e9e6b5126
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258149B2

Reaction notes

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