Hydrochloric Acid → [(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol

HRID 217991Notes

Reaction equation

HRID 217991 reaction equation
Cl.C([O:9][CH2:10][C@@H:11]1[O:20][CH2:19][C@@:18]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C@H:13]([CH2:14][S:15][C:16]([NH2:28])=[N:17]2)[CH2:12]1)C1C=CC=CC=1.[OH-].[Na+]>>[NH2:28][C:16]1[S:15][CH2:14][C@H:13]2[C@:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])([CH2:19][O:20][C@@H:11]([CH2:10][OH:9])[CH2:12]2)[N:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59281170(4aR,6R,8aS)-6-benzyloxymethyl-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine

Product 1

HCID 58406040[(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanolYield 92.1%

Procedure

Concentrated hydrochloric acid (25.2 ml) was added to (4aR,6R,8aS)-6-benzyloxymethyl-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine (1.26 g), and the mixture was heated under reflux for two hours. After cooling the reaction solution to room temperature, the reaction mixture was poured into ice. The mixture was neutralized with 5 N sodium hydroxide, and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual solid was washed with a mixed solvent of heptane and ether to obtain the title compound (890 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for two hours
  3. additionthe reaction mixture was poured into ice
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residual solid was washed with a mixed solvent of heptane and ether

Sources & evidence

ORD record
ord-4925a051a39b402bb48213693ce947fc
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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