Hydrochloric Acid → HCID 68676874, compound

HRID 644030Notes

Reaction equation

HRID 644030 reaction equation
C(OC([N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][C@H:9]1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=O)(C)(C)C.Cl>C(O)C>[CH:18]1([C@H:9]2[NH:8][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][CH2:10]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68674938HCID 68674938, compound

Product 1

HCID 68676874HCID 68676874, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (R)-4-tert-butoxycarbonyl-3-cyclohexyl-3,4-dihydro-2H-1,4-benzoxazine (3.98 g, 12.5 mmol), 5 N hydrochloric acid (10 ml) and ethanol (10 ml) was stirred at 70° C. for 50 min. Ethanol was removed in vacuo and the residue was partitioned between dichloromethane and 2 N sodium hydroxide solution. The aqueous layer was extracted with dichloromethane and combined organic layers were washed with brine, dried over sodium sulfate and concentrated to afford (R)-3-cyclohexyl-3,4-dihydro-2H-1,4-benzoxazine (2.72 g, 12.5 mmol).

Workup

  1. customEthanol was removed in vacuo
  2. customthe residue was partitioned between dichloromethane and 2 N sodium hydroxide solution
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwere washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c20eea6fd184e8090d15e9c43ab94f0
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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