HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methanesulfonic Acid → trans-10-fluoro-4-isopropyl-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine methanesulfonate

HRID 35366
Notes
Print preview

Reaction equation

HRID 35366 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:10]1[C:15](=O)[CH2:14][O:13][C@@H:12]2[C:17]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:18]=3[O:19][CH2:20][CH2:21][C@@H:11]12)([CH3:9])[CH3:8].[OH-].[Na+].[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>O1CCCC1.CCOCC>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[F:26][C:24]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][CH2:21][C@@H:11]3[C@H:12]([O:13][CH2:14][CH2:15][N:10]3[CH:7]([CH3:9])[CH3:8])[C:17]=2[CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 14256316HCID 14256316, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86742371trans-10-fluoro-4-isopropyl-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine methanesulfonate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2.1 g of lithium aluminum hydride in 200 ml of tetrahydrofuran was added 6.06 g of trans-4a,5,6,11b-tetrahydro-4-isopropyl-10-fluoro-2H-[1]benzoxepino[5,4-b]-1,4-oxazin-3(4H)-one in portions and the mixture was then refluxed for about one hour. The mixture was then cooled in ice, decomposed by the addition of 6 ml of 10% aqueous sodium hydroxide solution, and stirred for 16 hours. The solids present in the reaction mixture were separated by filtration and washed with water and the solvent was evaporated from the filtrate to leave a residual oil. The oil was dissolved in ether and a solution of methanesulfonic acid in ether was added until no more cloudiness occurred on addition. The solid was then separated by filtration and triturated in ether to give a tacky solid. This solid was recrystallized from a mixture of methanol and ethyl acetate to give trans-10-fluoro-4-isopropyl-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine methanesulfonate melting at about 163°-165° C.

Workup

  1. temperaturethe mixture was then refluxed for about one hour
  2. temperatureThe mixture was then cooled in ice
  3. customThe solids present in the reaction mixture were separated by filtration
  4. washwashed with water
  5. customthe solvent was evaporated from the filtrate
  6. customto leave a residual oil
  7. additionoccurred on addition
  8. customThe solid was then separated by filtration
  9. customtriturated in ether
  10. customto give a tacky solid
  11. customThis solid was recrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-761fad66ef044db886d595e5d1f25a80
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766212

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes