Aluminium lithium hydride → HCID 42597686, compound

HRID 1958527Notes

Reaction equation

HRID 1958527 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:26](OC)=[O:27])=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:8]2[C:17]=1[CH2:16][C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:9]2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>ClCCl.C(OCC)C>[OH:27][CH2:26][C:6]1[C:5]([CH2:3][OH:2])=[C:17]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N:8]2[C:7]=1[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68918010HCID 68918010, compound

Product 1

HCID 42597686HCID 42597686, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the 3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-dicarboxylic acid dimethyl ester (3.91 g, 10 mmol) in anhydrous dichloromethane (20 mL) was added dropwise to a stirred suspension of LiAlH4 (0.87 g, 23 mmol) in anhydrous diethyl ether (30 mL) at 10-15° C. The reaction mixture was further stirred for 2 hours after the addition was completed. The mixture was cooled in an ice bath and the excess hydride was destroyed by the sequential addition of water (1.2 mL), 15% aqueous NaOH (1.2 mL), and water (3.6 mL) at 0° C. The inorganic salt was removed by filtration, was washed with hot THF (300 mL), and the combined filtrate and washings was evaporated under reduced pressure to dryness. The solid residue was recrystallized from dichloromethane/ether to give [2-hydroxymethyl-3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]-isoquinolin-1-yl]methanol (DA-1106), 2.29 g (68.4%); mp 174-176° C.; 1H NMR (DMSO-d6) δ 3.82 (3H, s, OMe), 4.05 (2H, s, CH2), 4.26 (2H, d, J=5.0 Hz, CH2), 4.45-4.54 (4H, m, CH2 and exchangeable, 2×OH), 4.93 (2H, s, CH2), 7.05 (2H, d, J=8.4 Hz, ArH), 7.17-7.21 (1H, m, ArH), 7.25-7.28 (2H, m, ArH), 7.38 (2H, d, J=8.4 Hz, ArH), 7.37-7.39 (1H, m, ArH); m/z 451.9 (M+H)+ Anal. Calcld. for C21H21NO3 0.2H2O: C, 74.40; H, 6.36; N, 4.13. Found: C, 74.41; H, 6.30; N, 4.13.

Workup

  1. additionafter the addition
  2. temperatureThe mixture was cooled in an ice bath
  3. customthe excess hydride was destroyed by the sequential addition of water (1.2 mL), 15% aqueous NaOH (1.2 mL), and water (3.6 mL) at 0° C
  4. customThe inorganic salt was removed by filtration
  5. washwas washed with hot THF (300 mL)
  6. customthe combined filtrate and washings was evaporated under reduced pressure to dryness
  7. customThe solid residue was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-40b58af2c6b6407a8e6a05709024cb1f
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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