Water → HCID 9924971, compound

HRID 1633452Notes

Reaction equation

HRID 1633452 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]4[O:26][C:25]([CH3:28])([CH3:27])[CH:24]=[CH:23][C:18]4=3)[NH:13][C:12]=2[CH2:11][CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]4[O:26][C:25]([CH3:28])([CH3:27])[CH:24]=[CH:23][C:18]4=3)[NH:13][C:12]=2[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18679309HCID 18679309, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9924971HCID 9924971, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-benzoyl-3,3-dimethyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.115 g, 0.31 mmol) in tetrahydrofuran (5.0 mL) was added lithium aluminum hydride (0.125 g, 3.10 mmol). The resulted mixture was stirred at room temperature for 16 h. Water (0.13 mL), 15% sodium hydroxide solution (0.13 mL) and water (0.39 mL) were added sequentially. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to dryness. The residue was subjected to prep TLC (25% EtOAc/hexane, 1% Et3N) to afford 0.067 g (60%) of light yellow solid as the title compound: 1H NMR (300 MHz, CDCl3) δ 7.68, 7.47-7.30, 7.06-7.02, 6.69, 5.63, 3.85, 3.18-3.16, 3.05-2.88, 1.49; 13C NMR (DMSO-d6) δ 147.3, 139.5, 138.2, 130.8, 129.4, 129.2, 128.7, 127.5, 124.7, 120.9, 113.5, 113.2, 111.9, 110.0, 75.0, 61.4, 55.8, 54.0, 28.6, 27.4, 26.2; MS (ESI+) m/z 373 (M++H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-65d4a7a2341d48389c8d1e0ea6ea92be
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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