Sodium hydride → Butyl 3-amino-6-benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine-2-carboxylate

HRID 1648941Notes

Reaction equation

HRID 1648941 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][OH:3].[H-].[Na+].[CH2:12]([N:19]1[CH2:25][CH2:24][C:23]([C:26]#[N:27])=[C:22](Cl)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1>[NH2:27][C:26]1[C:23]2[CH2:24][CH2:25][N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20][CH2:21][C:22]=2[O:3][C:2]=1[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81882Butyl GlycolateHCID 130720321-Benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine

Product 1

HCID 20481347Butyl 3-amino-6-benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 1.0 gm (0.008 mol) of butyl glycolate in 8 ml of absolute dioxane was added dropwise to a suspension of 0.4 gm (0.008 mol) of 50% sodium hydride in 5 ml of absolute dioxane, and the mixture was stirred for one hour at room temperature. Then, while the mixture was cooled with ice, a solution of 1.0 gm (0.004 mol) of 1-benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine in 15 ml of absolute dioxane was added, and the mixture was stirred for one hour. The reaction mixture was then poured into about 80 ml of ice-cold water, and the aqueous mixture was extracted three times with ethyl acetate. The combined organic phases were washed twice with water, dried over sodium sulfate and concentrated by evaporation. The residue was purified by column chromatography on silicagel, using toluene/ethyl acetate (7:3) as eluant.

Workup

  1. temperatureThen, while the mixture was cooled with ice
  2. stirringthe mixture was stirred for one hour
  3. extractionthe aqueous mixture was extracted three times with ethyl acetate
  4. washThe combined organic phases were washed twice with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-c641c795bc4f4bbb883ca4db35fce154
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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