Ethyl chloroformate → HCID 70514605, compound

HRID 1702753Notes

Reaction equation

HRID 1702753 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:21]([OH:22])=[CH:20][C:7]2[C@H:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[CH:5]=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(COC)OC>[ClH:3].[Cl:3][C:4]1[C:21]([O:22][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][C:7]2[C@H:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

Product 1

HCID 70514605HCID 70514605, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Add 480 mg (0.01 moles) of sodium hydride (50% in mineral oil) in small portions, to a stirred suspension of 2.88 g (0.01 moles) of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (obtained in step E of Example 1) in 60 ml of dry dimethoxyethane and stir until the evolution of gas ceases. Add dropwise a solution of 1.08 g (0.01 moles) of ethyl chloroformate in 10 ml of dimethoxyethane with stirring and then stir the reaction mixture at room temperature for 16 hours. Evaporate to dryness at 100° C. and treat the residue with a mixture of 50 ml each of water and ethyl ether. Dry the ether layer over anhydrous sodium sulfate and precipitate (S)-7-chloro-8-ethoxycarbonyloxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 196°-197° C., [α]D26 =+27.1° (c=1, dimethylformamide).

Workup

  1. stirringwith stirring
  2. stirringstir the reaction mixture at room temperature for 16 hours
  3. customEvaporate to dryness at 100° C.
  4. additiontreat the residue
  5. additionwith a mixture of 50 ml each of water and ethyl ether
  6. dry with materialDry the ether layer over anhydrous sodium sulfate
  7. customprecipitate (S)-7-chloro-8-ethoxycarbonyloxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride
  8. customObtain an analytical sample
  9. customby crystallization from 2-propanol, m.p. 196°-197° C., [α]D26 =+27.1° (c=1, dimethylformamide)

Sources & evidence

ORD record
ord-90346ddb1fe64b88b4c71618b2a5fff3
Source dataset
uspto-grants-1982_09
Patent number
US04349472

Reaction notes

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