Sodium borohydride → HCID 49806451, compound

HRID 2381191Notes

Reaction equation

HRID 2381191 reaction equation
[CH3:1][O:2][C:3]1[C:23]2[C:22]3([CH2:27][CH:26]=[CH:25][CH2:24]3)[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:28][CH3:29])=[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]3([CH2:27][CH2:26][CH2:25][CH2:24]3)[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:28][CH3:29])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 49806337HCID 49806337, compound

Product 1

HCID 49806451HCID 49806451, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9′,10′-dimethoxy-5′,6′,13′,13a′-tetrahydrospiro[cyclopent-3-ene-1,8′-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline] (300 mg, 0.75 mmol) in methanol (20 mL) was added sodium borohydride (57 mg, 1.5 mmol) in small portions at 25° C. After stirring at 25° C. for 2 h, the reaction solvent 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-5′,6′,13′,13a′-tetrahydrospiro [cyclopentane-1,8′-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline] (155 mg, 52%). LC/MS m/e calcd for C24H27NO4 (M+H)+: 394.49, observed: 394.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.80 (m, 2 H) 1.85-1.96 (m, 2 H) 1.96-2.08 (m, 2 H) 2.16-2.25 (m, 1 H) 2.25-2.35 (m, 1 H) 2.56-2.65 (m, 2 H) 2.65-2.71 (m, 2 H) 2.93-3.03 (m, 2 H) 3.78 (d, J=6.57 Hz, 6 H) 3.91 (d, J=7.83 Hz, 1 H) 5.94 (d, J=3.54 Hz, 2 H) 6.65 (s, 1 H) 6.73 (d, J=8.34 Hz, 1 H) 6.84 (s, 1 H) 6.88 (d, J=8.34 Hz, 1 H).

Workup

  1. concentrationthe reaction solvent 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-8efd2584db494b24b4ae991b61581be7
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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