Sodium borohydride → HCID 178490882, compound

HRID 1370141Notes

Reaction equation

HRID 1370141 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[N:7]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:8](=[O:21])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]=[O:20])[CH:12]=3)[C:5]=2[CH:4]=1)#[N:2].[BH4-].[Na+]>C(O)C.O1CCCC1>[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[N:7]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:8](=[O:21])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH2:19][OH:20])[CH:12]=3)[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178490881HCID 178490881, compound

Product 1

HCID 178490882HCID 178490882, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-cyano-3-(3-formyl-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-1,3-dihydro-2H-benzimidazol-2-one (35.0 mg) in a mixture of ethanol (2 mL) and tetrahydrofuran (1 mL) was added sodium borohydride (3.27 mg) under ice cooling, and the mixture was stirred at 0° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with 1N-hydrochloric acid, water, saturated sodium bicarbonate solution and brine, successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by a preparative silica gel column chromatography eluting with a mixture of chloroform and methanol (10:1). The crude product was triturated with diisopropyl ether to give 5-cyano-1-(trans-4-hydroxycyclohexyl)-3-(3-hydroxymethyl-4-methoxybenzyl)-1,3-dihydro-2H-benzimidazol-2-one as a colorless powder (20.0 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with 1N-hydrochloric acid, water, saturated sodium bicarbonate solution and brine
  3. dry with materialsuccessively, dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by a preparative silica gel column chromatography
  6. washeluting with a mixture of chloroform and methanol (10:1)
  7. customThe crude product was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-d98fad05e7ff414fb894c4c5783a7351
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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