Sodium Hydroxide → (Rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1h-isoindole-1,3(2h)-dione

HRID 2179903Notes

Reaction equation

HRID 2179903 reaction equation
C([BH3-])#N.[Na+].[O:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[C:10]([CH2:17][N:18]2[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]2=[O:28])=[CH:9][N:8]3[CH2:7][CH2:6]1.[OH-].[Na+]>CO.C(O)(C(F)(F)F)=O.O>[O:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH:10]([CH2:17][N:18]2[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]2=[O:28])[CH2:9][N:8]3[CH2:7][CH2:6]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 224889862-(2,3-Dihydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1h-isoindole-1,3(2h)-dione

Product 1

HCID 22488989(Rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1h-isoindole-1,3(2h)-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A freshly prepared solution of sodium cyanoborohydride (0.093 g, 1.48 mmol) in CH3OH (0.3 mL) was added dropwise to a 0° C. solution of 2-(2,3-dihydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.094 g, 0.29 mmol) in TFA (3.0 mL). The mixture was stirred at rt for 1 hour and diluted with H2O (10.0 mL) and made basic by the addition of 15% NaOH. The mixture was then extracted with EtOAc (3×). The combined EtOAc solution was dried over MgSO4 and concentrated in vacuo to dryness. The residue was redissolved in CH2Cl2 and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to preparative TLC (EtOAc/Hex., ½) to give 0.031 g (33%) of light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.93-7.88 (m, 2 H), 7.80-7.75 (m, 2 H), 6.79-6.77 (m, 1 H), 6.75-6.65 (m, 2 H), 4.46-4.43 (m, 2 H), 4.10-4.05 (m, 1 H), 4.00-3.94 (m, 1 H), 3.77-3.73 (m, 1 H), 3.34-3.33 (m, 1 H), 3.30-3.26 (m, 1 H), 3.17-3.15 (m, 1 H), 3.10-3.08 (m, 1 H); MS (EI) m/z 321 (M++H).

Workup

  1. extractionThe mixture was then extracted with EtOAc (3×)
  2. dry with materialThe combined EtOAc solution was dried over MgSO4
  3. concentrationconcentrated in vacuo to dryness
  4. dissolutionThe residue was redissolved in CH2Cl2
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-d51714ddf84d4f789ccfff83414cfbf6
Source dataset
uspto-grants-2005_05
Patent number
US06887868B2

Reaction notes

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