Diethyl Ether → HCID 86684374, compound

HRID 592850Notes

Reaction equation

HRID 592850 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=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+].C(OCC)C>CO.[Cl-].[Zn+2].[Cl-].O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][CH2:19][N:20]([CH:25]4[CH2:26][O:23][CH2:24]4)[CH2:21][CH:22]=3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86684373HCID 86684373, compound

Product 1

HCID 86684374HCID 86684374, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 200d (500 mg, 1.4 mmol), oxetan-3-one (298 mg, 4.2 mmol), NaBH3CN (261 mg, 4.2 mmol), and 1 mol/L zinc chloride in ethoxyethane (4 mL, 4.2 mmol) in methanol (20 mL) was stirred at 50° C. for 5 hours. Water (20 mL) was added to the reaction and the resulting mixture was extracted with dichloromethane (3×50 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 10:1 methylene chloride/methanol to afford 200e (450 mg, 78%) as a yellow solid. MS-ESI: [M+H]+ 419.1

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (3×50 mL)
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica-gel column chromatography
  4. washeluting with 10:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-174798e899774d6fb119207d9aff4362
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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