Cyclohexane → HCID 59599682, compound

HRID 2266642Notes

Reaction equation

HRID 2266642 reaction equation
[F:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:4][C:3]=1[CH:15]=O.[NH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1.[BH3-]C#N.[Na+].C1CCCCC1>CO.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:4][C:3]=1[CH2:15][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8078CyclohexaneHCID 694601,2,3,4-TetrahydroquinolineHCID 5003444Sodium cyanoborohydrideHCID 59599685HCID 59599685, compound

Product 1

HCID 59599682HCID 59599682, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbaldehyde (202 mg) at room temperature in methanol (10 ml) under an argon atmosphere were added zinc chloride (409 mg) and 1,2,3,4-tetrahydroquinoline (100 mg). The clear light yellow solution was stirred for 4 hours and 30 minutes. Then, NaBH3CN (141 mg) was added in one portion. The mixture was heated to 60° C. and stirring at that temperature was continued for 22 hours. The reaction was directly adsorbed on silica gel. The crude product was isolated by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/ethyl acetate 65:35) to give 1-[5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-ylmethyl]-1,2,3,4-tetrahydroquinoline (238 mg) as colorless viscous oil. MS (ISP): 362.3 ([M+H]+).

Workup

  1. stirringstirring at that temperature
  2. waitwas continued for 22 hours

Sources & evidence

ORD record
ord-55fff2bb26e44164ad724501b0b19ba0
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

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