1-(1,1-Dimethylethyl) 2-(phenylmethyl) 2-azabicyclo[3.1.0]hexane-1,2-dicarboxylate → HCID 15927972, compound

HRID 1031321Notes

Reaction equation

HRID 1031321 reaction equation
C([N:11]1[CH2:15][CH2:14][CH:13]2[CH2:16][C:12]12[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(OCC1C=CC=CC=1)=O>C(OCC)(=O)C>[NH:11]1[CH2:15][CH2:14][CH:13]2[CH2:16][C:12]12[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

3

Reactant 1

HCID 159279711-(1,1-Dimethylethyl) 2-(phenylmethyl) 2-azabicyclo[3.1.0]hexane-1,2-dicarboxylate

Product 1

HCID 15927972HCID 15927972, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound (5) was dissolved in ethyl acetate (300 ml) and the solution was flushed with argon. Palladium-on-carbon (5%, 3 g) was added and hydrogen was bubbled into the stirred suspension until no starting material remained (2 hours as indicated by TLC). The flask was then flushed with nitrogen and the catalyst was removed by filtration. The catalyst was washed with methanol (3×100 ml) and the combined filtrates were concentrated. The residue was then distilled with a Kuglerohr apparatus at reduced pressure to give 6.6 g (85%) of compound (6) as a light yellow oil: bp=90°-120° C./0.8 mm; 1H NMR (C6D6): δ2.83 (m, 1H), 2.32 (m, 1H), 2.10 (br s, 1H), 1.76 (m, 1H), 1.3-1.65 (m, 3H), 1.36 (s, 9H), 0.85 (t, J=6 Hz) ppm. 13NMR (C6D6) δ172.2 (C=O), 80.1 (quat), 50.1 (quat), 44.3 (CH2), 28.1 (CH2), 27.7 (CH), 16.7 (CH2) ppm.

Workup

  1. customthe solution was flushed with argon
  2. additionPalladium-on-carbon (5%, 3 g) was added
  3. customhydrogen was bubbled into the stirred suspension until no starting material
  4. custom(2 hours as indicated by TLC)
  5. customThe flask was then flushed with nitrogen
  6. customthe catalyst was removed by filtration
  7. washThe catalyst was washed with methanol (3×100 ml)
  8. concentrationthe combined filtrates were concentrated
  9. distillationThe residue was then distilled with a Kuglerohr apparatus at reduced pressure

Sources & evidence

ORD record
ord-c15f25dc981f4256892590601d7602a2
Source dataset
uspto-grants-1990_09
Patent number
US04954158

Reaction notes

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