Sodium cyanoborohydride → HCID 86684344, compound

HRID 592789Notes

Reaction equation

HRID 592789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[N:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[O:23]1[CH2:26][C:25](=O)[CH2:24]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[N:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([CH:25]4[CH2:26][O:23][CH2:24]4)[CH2:21][CH2:22]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86684343HCID 86684343, compound

Product 1

HCID 86684344HCID 86684344, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 189f (740 mg, 2.0 mmol), oxetan-3-one (288 mg, 4.0 mmol), NaBH3CN (315 mg, 5.0 mmol), and zinc chloride (680 mg, 5.0 mmol) in methanol (60 mL) was stirred at 50° C. for 5 hours. It was then quenched with water and concentrated under reduced pressure. The residue was extracted with dichloromethane three times. The combined extract was concentrated under reduced pressure to afford crude 189g as a yellow solid (660 mg, 78%), which was used in the next step without further purification. MS: [M+H]+ 423.1.

Workup

  1. customIt was then quenched with water
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane three times
  4. extractionThe combined extract
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6b079af932f470e860a02da56f6fb8f
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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