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

HRID 588703Notes

Reaction equation

HRID 588703 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-f6efe5744a574407ab3d757ebab5d6d0
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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