Aluminium lithium hydride → HCID 56945246, compound

HRID 2369340Notes

Reaction equation

HRID 2369340 reaction equation
[CH3:1][C:2]1[N:18]2[C:5]([CH2:6][C:7]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH3:16])[C:8]=3[CH2:17]2)=[C:4]([C:19](OC)=[O:20])[C:3]=1[C:23](OC)=[O:24].[H-].[H-].[H-].[H-].[Li+].[Al+3]>ClCCl.C(OCC)C>[CH3:1][C:2]1[N:18]2[C:5]([CH2:6][C:7]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH3:16])[C:8]=3[CH2:17]2)=[C:4]([CH2:19][OH:20])[C:3]=1[CH2:23][OH:24]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71574456HCID 71574456, compound

Product 1

HCID 56945246HCID 56945246, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 3,6-dimethyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate (3.5 g, 10.0 mmol) in anhydrous dichloromethane (35 mL) was added dropwise into a stirred suspension of LiAlH4 (0.9 g, 25.0 mmol) in anhydrous diethyl ether (20 mL) at 0 to −5° C. The reaction mixture was further stirred for 15 min after the addition was completed. The excess hydride was destroyed by the sequential addition of water (1 mL), 15% aqueous NaOH (1 mL), and water (1 mL) at 0° C. The mixture was filtered through a pad of Celite, the solid residue was washed with dichloromethane. The combined filtrate and washings were evaporated to dryness in vacuo. The residue was triturated with ether to give [3,6-dimethyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-diyl]dimethanol (BO-1922), 2.3 g (79%); mp 200-201° C. 1H NMR (DMSO-d6) δ 2.29 (3H, s, Me), 3.73 (3H, s, Me), 3.99 (2H, s, CH2), 4.38 (4H, brs, CH2 and exchangeable, OH), 4.44 (2H, s, CH2), 5.13 (2H, s, CH2), 7.05 (1H, t, J=7.4 Hz, ArH), 7.16 (1H, t, J=7.4 Hz, ArH), 7.46 (1H, d, J=7.8 Hz, ArH), 7.53 (1H, d, J=7.8 Hz, ArH). Anal. Calcd for (C18H20N2O2.0.5H2O): C, 70.80; H, 6.93; N, 9.17. Found: C, 70.85; H, 6.65; N, 9.02.

Workup

  1. additionafter the addition
  2. customThe excess hydride was destroyed by the sequential addition of water (1 mL), 15% aqueous NaOH (1 mL), and water (1 mL) at 0° C
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washthe solid residue was washed with dichloromethane
  5. customThe combined filtrate and washings were evaporated to dryness in vacuo
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-a80252689bd34958a5d663d5480b9b11
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

Loading…