Sodium borohydride → HCID 19036248, compound

HRID 52969Notes

Reaction equation

HRID 52969 reaction equation
[BH4-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:8]([C:17]#[N:18])=[C:9]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=1)[CH2:4][CH3:5]>C(O)C.O1CCCC1>[OH:16][CH:11]([C:9]1[N:10]=[C:6]([CH2:3][CH2:4][CH3:5])[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:35]=[N:34][N:33]=3)=[CH:24][CH:25]=2)[C:8]=1[C:17]#[N:18])[C:12]([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 217408232-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

Product 1

HCID 19036248HCID 19036248, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 108 mg of sodium borohydride in 20 ml of ethanol was added to a solution of 2.00 g of 2-propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile [prepared as described in step (a) above] in 40 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2.5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane, to give 1.93 g of the title compound as crystals, melting at 115°-117° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe syrupy residue was crystallized in a 1:4 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4d5d9b06a7144ca79a676f564c8b5a52
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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