1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68723174, compound

HRID 1471391Notes

Reaction equation

HRID 1471391 reaction equation
C(O[C@@H:5]1[CH2:14][C:9]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[C@@H:8]([C:15]([O:17][CH2:18]C)=[O:16])[C:7]([CH3:20])=[CH:6]1)(=O)C.C1CCN2C(=NCCC2)CC1>Cl>[CH3:20][C:7]1[CH:6]=[CH:5][CH2:14][C:9]2([CH2:10][CH2:11][CH2:12][CH2:13]2)[C:8]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131732746HCID 131732746, compound

Product 1

HCID 68723174HCID 68723174, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of a 30:70 mixture of cis-/trans-ethyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (2.7 g, 9.6 mmol) in DBU (15 ml, 97 mmol) was stirred for 4 d at 20° C. The reaction mixture was poured into cold 2N aqueous HCl (50 ml), and extracted twice with MTBE (50 ml). The combined organic phases were washed with 2N aqueous HCl (30 ml), with water (40 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4), and concentrated. FC (250 g SiO2, pentane/Et2O 100:1) of the crude product (1.8 g) gave methyl 7-methylspiro[4.5]deca-6,8-diene-6-carboxylate (0.54 g, 25%).

Workup

  1. extractionextracted twice with MTBE (50 ml)
  2. washThe combined organic phases were washed with 2N aqueous HCl (30 ml), with water (40 ml), with a saturated aqueous solution of NaCl (40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8b3342a332046a0abb7d1e6606bac9b
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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