Ethyl Acetate → Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 336627Notes

Reaction equation

HRID 336627 reaction equation
[O:1]1[CH2:3][C:2]21[CH2:9][CH:8]1[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:5]([CH2:6][CH2:7]1)[CH2:4]2.C([O-])(O)=O.[Na+].C(OCC)(=O)C>O1CCCC1>[CH:3]([CH:2]1[CH2:4][CH:5]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH:8]([CH2:7][CH2:6]2)[CH2:9]1)=[O:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 74394144Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate

Product 1

HCID 51030438Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

To a cold (0° C.) solution of EXAMPLE 84A (3.5 g) in tetrahydrofuran (40 mL) was added boron trifluoride diethyl ether complex (0.82 mL). The mixture was stirred at 3-5° C. for 3 hours. Aqueous saturated NaHCO3 was added, followed by ethyl acetate (200 mL). The organic layer was separated, washed with water (twice) and concentrated to dryness. Toluene was added and the mixture was concentrated under vacuum to provide the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (twice) and
  3. concentrationconcentrated to dryness
  4. additionToluene was added
  5. concentrationthe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-19222742187240558bbb5ec36574dc5c
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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