Water → HCID 59263478, compound

HRID 545950Notes

Reaction equation

HRID 545950 reaction equation
[CH2:1]([N:6]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:8]2([CH2:20]C[C:18](=[O:21])[C:17]3[C:9]2=[CH:10][C:11]2[O:15][CH2:14][O:13][C:12]=2[CH:16]=3)[C:7]1=[O:28])[CH2:2][CH2:3][CH2:4][CH3:5].[BH4-].[Na+].O>CO>[OH:21][CH:18]1[C:17]2[C:9](=[CH:10][C:11]3[O:15][CH2:14][O:13][C:12]=3[CH:16]=2)[C:8]2([C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2=[O:28])[CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 545845861-pentyl-6''H-spiro[indoline-3,5''-naphtho[2,3-d][1,3]dioxole]-2,8''(7''H)-dione

Product 1

HCID 59263478HCID 59263478, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-pentyl-6′H-spiro[indole-3,5′-naphtho[2,3-d][1,3]dioxole]-2,8′(1H,7′H)-dione (0.20 g, 0.55 mmol) in methanol (10.0 mL) was added sodium borohydride (0.03 g, 0.83 mmol). The reaction mixture was stirred at ambient temperature for 2 h and poured into of water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.18 g, 90%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.36-7.29 (m, 1H), 7.11-6.99 (m, 3H), 6.93 (d, 1H), 5.98 (s, 1H), 5.94-5.87 (m, 2H), 5.16 (d, 1H), 3.80-3.61 (m, 2H), 2.69 (br, 1H), 2.39 (d, 1H), 1.75-1.62 (m, 2H), 1.38-1.22 (m, 4H), 0.87 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 180.5, 148.9, 148.5, 143.7, 140.5, 136.9, 132.1, 128.7, 123.7, 123.3, 108.8, 105.7, 103.2, 101.5, 74.8, 59.6, 40.4, 28.9, 27.0, 22.3, 14.0; MS (ES+) m/z 388.4 (M+23).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-9c5dc0a34fb741e9ac6590b9a771f421
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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