Bromide ion → HCID 49806336, compound

HRID 2381216Notes

Reaction equation

HRID 2381216 reaction equation
[CH2:1]([CH:8]1[CH:17]2[C:18]3[C:23]([CH2:24][CH2:25][NH+:16]2[C:15]([CH3:30])([CH3:29])[C:14]2[C:13]([O:31][CH3:32])=[C:12]([O:33][CH3:34])[CH:11]=[CH:10][C:9]1=2)=[CH:22][C:21]1[O:26][CH2:27][O:28][C:20]=1[CH:19]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[BH4-].[Na+]>CO>[CH2:1]([CH:8]1[CH:17]2[C:18]3[C:23]([CH2:24][CH2:25][N:16]2[C:15]([CH3:30])([CH3:29])[C:14]2[C:13]([O:31][CH3:32])=[C:12]([O:33][CH3:34])[CH:11]=[CH:10][C:9]1=2)=[CH:22][C:21]1[O:26][CH2:27][O:28][C:20]=1[CH:19]=3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 4311764Sodium borohydrideHCID 86647498HCID 86647498, compound

Product 1

HCID 49806336HCID 49806336, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 13-benzyl-9,10-dimethoxy-8,8-dimethyl-5,6,8,13-tetrahydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; bromide (100 mg, 0.19 mmol) in methanol (10 mL) was added sodium borohydride (14 mg, 0.38 mmol) in small portions at 25° C. After stirring at 25° C. for 10 min, 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 13-benzyl-9,10-dimethoxy-8,8-dimethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (64 mg, 73%). LC/MS m/e calcd for C29H31NO4 (M+H)+: 458.57, observed: 458.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (s, 3 H) 1.64 (s, 3 H) 2.34-2.49 (m, 2 H) 2.53-2.68 (m, 2 H) 2.75-2.85 (m, 1 H) 3.11-3.16 (m, 1 H) 3.26-3.31 (m, 1 H) 3.72 (s, 3 H) 3.80 (s, 3 H) 4.14 (s, 1 H) 5.94-5.99 (m, 3 H) 6.64 (d, J=8.34 Hz, 1 H) 6.69 (s, 1 H) 6.76 (d, J=7.07 Hz, 2 H) 6.94 (s, 1 H) 7.06-7.17 (m, 3 H).

Workup

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

Sources & evidence

ORD record
ord-8701dd7c382f4a3a80f2a9fe40dd84cb
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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