HCID 59352564, compound → HCID 46194440, compound

HRID 1407941Notes

Reaction equation

HRID 1407941 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:28]4[C:19](=[CH:20][C:21]5[O:26][CH2:25][CH2:24][O:23][C:22]=5[CH:27]=4)[O:18][CH2:17]3)[C:9]2=[O:29])[CH2:4][O:3]1>C(O)(=O)C.O>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2([C:28]3[C:19](=[CH:20][C:21]4[O:26][CH2:25][CH2:24][O:23][C:22]=4[CH:27]=3)[O:18][CH2:17]2)[C:9]1=[O:29]

Participants

4

Reactant 1

HCID 59352564HCID 59352564, compound

Product 1

HCID 46194440HCID 46194440, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1′-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.66 g, 1.61 mmol) in glacial acetic acid (10 mL) and water (5 mL) was stirred at ambient temperature for 18 h and concentrated in vacuo. The residue was recrystallized from ethyl acetate to afford 1′-[(2S)-2,3-dihydroxypropyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.59 g, 99%): mp 179-181° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 7.30-7.25 (m, 1H), 7.13-7.07 (m, 2H), 7.01-6.95 (m, 1H), 6.46 (s, 1H), 6.21-6.19 (m, 1H), 5.02-4.94 (m, 1H), 4.71-4.57 (m, 3H), 4.14-4.06 (m, 4H), 3.81-3.54 (m, 3H), 3.39-3.32 (m, 2H); MS (ES+) m/z 369.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e8e751706cdb461689251e11f7199754
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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