1,2-Dimethoxyethane → HCID 54094583, compound

HRID 1491628Notes

Reaction equation

HRID 1491628 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COCCOC.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[NH:23][C:22](=O)[C@H:21]([CH3:25])[NH:20][C:19](=O)[C:18]=2[CH:27]=1.[OH-].[Na+]>O.O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[NH:23][CH2:22][C@H:21]([CH3:25])[NH:20][CH2:19][C:18]=2[CH:27]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 15169699HCID 15169699, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 54094583HCID 54094583, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) suspension of 8.53 parts of lithium aluminum hydride in 392 parts of 1,2-dimethoxyethane there were added dropwise 20.19 parts of (S)-7-chloro-3,4-dihydro-3-methyl-1H-1,4-benzodiazepine-2,5-dione (prepared as intermediate 43) under argon. The mixture was left at room temperature for 3 hours and was then refluxed for 29 hours. After cooling to 0° C., there were added successively a mixture of 8.5 parts of water and 22.7 parts of tetrahydrofuran, 9.86 parts of NaOH (15%) and 25.5 parts of water. The whole was stirred for 24 hours and was then filtered. The precipitate was refluxed in 178 parts of tetrahydrofuran for 5 min and filtered off again. The combined filtrates were evaporated and the residual oil crystallized on standing, yielding 18.4 parts (100%) of (S)-7-chloro-2,3,4,5-tetrahydro-3-methyl-1H-1,4-benzodiazepine (interm. 59).

Workup

  1. temperatureTo a cooled
  2. temperaturewas then refluxed for 29 hours
  3. additionthere were added successively
  4. filtrationwas then filtered
  5. temperatureThe precipitate was refluxed in 178 parts of tetrahydrofuran for 5 min
  6. filtrationfiltered off again
  7. customThe combined filtrates were evaporated
  8. customthe residual oil crystallized

Sources & evidence

ORD record
ord-a99b80c4990b4c8a810b842a7d78005e
Source dataset
uspto-grants-1994_12
Patent number
US05371079

Reaction notes

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