HCID 15222104, compound → HCID 18962500, compound

HRID 1707763Notes

Reaction equation

HRID 1707763 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:51][CH2:52][CH3:53])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:9]=1[C:10](OC)=[O:11])(OC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:1][C:5]1[N:6]=[C:7]([CH2:51][CH2:52][CH3:53])[N:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 15222104HCID 15222104, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18962500HCID 18962500, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dicarbomethoxy-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole (9.88 g, 14.1 mmol, 1 eq) was dissolved in a minimum of THF and to this solution, lithium aluminum hydride (1.0M in THF) (15.48 mL, 15.48 mmol, 1.1 eq) was slowly added dropwise. The mixture was allowed to stir at room temperature overnight after which It was quenched by the Steinhardt procedure (Fieser & Fieser V.1, p.584) as follows: to the reaction mixture water (0.66 mL) was first carefully added followed by 15% NaOH (0.66 mL) followed by water (1.97 mL). After stirring for 72 h, a very fine suspension of particulate had formed which was slowly filtered through Celite™. The filtrate was dried (MgSO4) and the solvent removed in vacuo to yield 8.83 g of a yellow glass which could not be recrystallized. This Intermediate was suitable for further transformation. NMR (DMSO-d6) δ 7.82 (d, 1H,J=9Hz); 7.68-7.28 (m,12H); 7.05 (d,2H,J=9Hz); 6.87 (d,6H,J=9Hz); 5.16 (s,2H); 4.94 (t,1H,J=7Hz); 4.66 (t,1H,J=7Hz); 4.37 (d,2H,J=7Hz); 4.32 (d,2H,J=7Hz); 2.34 (t,2H,J=7Hz); 1.52 (t of q,2H,J=7,7Hz); 0.77 (t,3H,J=7Hz). IR (neat) 3300 br; 3061; 1027; 1006; 909; 732; 699 cm-1. Anal. calcd. for C41H38N6O2.H2O: C, 74.07; H, 6.06; N, 12.64. Found: C, 74.06; H, 5.95: N, 11.86.

Workup

  1. additionwas slowly added dropwise
  2. customwas quenched by the Steinhardt procedure (Fieser & Fieser V.1, p.584)
  3. additionto the reaction mixture water (0.66 mL) was first carefully added
  4. stirringAfter stirring for 72 h
  5. additiona very fine suspension of particulate
  6. customhad formed which
  7. filtrationwas slowly filtered through Celite™
  8. dry with materialThe filtrate was dried (MgSO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-000c52e34df64d7abda2a6c64a321b7d
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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