Isopropyl iodide → HCID 57424222, compound

HRID 2377355Notes

Reaction equation

HRID 2377355 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH:16]=O)[CH:15]=1)[O:12][C:11]([CH3:19])([CH3:18])[CH2:10][C:9]2([CH3:21])[CH3:20])=[O:5])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+].[CH:36](I)([CH3:38])[CH3:37]>ClCCl.C(#N)C.CC(C)=O.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH2:16][N:25]([CH:22]3[CH2:24][CH2:23]3)[CH:36]([CH3:38])[CH3:37])[CH:15]=1)[O:12][C:11]([CH3:19])([CH3:18])[CH2:10][C:9]2([CH3:21])[CH3:20])=[O:5])[CH3:2]

Participants

10

Reactant 5

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 57424221HCID 57424221, compound2×

Product 1

HCID 57424222HCID 57424222, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Following General Procedure C and using 8-formyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid ethyl ester (Intermediate 37, 0.11 g, 0.23 mmol) in dichloromethane (4 mL) and acetonitrile (2 mL), cyclopropyl amine (0.08 mL, 1.1 mmol), acetic acid (0.8 mL) and sodium cyanoborohydride (0.072 g, 1.1 mmol) followed by work up and flash column chromatography afforded an intermediate. The intermediate (0.122 g, 0.22 mmol) was dissolved in acetone (10 mL) and treated with potassium carbonate (0.153 g, 1.1 mmol) and isopropyl iodide (0.04 mL). The resulting reaction mixture was at 60° C. for 4 h. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. Flash column chromatography over silica gel (230-400 mesh) using 15-20% ethyl acetate in hexane as the eluent afforded the title compound (0.09 g, 71%) as a clear oil.

Workup

  1. customflash column chromatography afforded an intermediate
  2. customThe resulting reaction mixture
  3. customThe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to an oil

Sources & evidence

ORD record
ord-1af86e3c734f4871ba3357c0fea39197
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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