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

HRID 1471395Notes

Reaction equation

HRID 1471395 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][CH3:18])=[O:16])[C:7]([CH3:19])=[CH:6]1)(=O)C.C1CCN2C(=NCCC2)CC1>Cl>[CH3:19][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 131732748HCID 131732748, compound

Product 1

HCID 68723174HCID 68723174, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

A part of the crude trans-methyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate obtained (2.4 g) was dissolved in DBU (13 g, 85.6 mmol) and stirred for 21 h at 20° C. and for 7 h at 40° C. The reaction mixture was poured into cold 2N aqueous HCl (60 ml), and extracted twice with cyclohexane (50 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (500 g SiO2, pentane/Et2O 100:1) of the crude product (1.47 g) gave methyl 7-methylspiro[4.5]deca-6,8-diene-6-carboxylate (0.77 g, 13% estimated overall yield). Boiling point: 100° C. (0.08 mbar).

Workup

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

Sources & evidence

ORD record
ord-7d1e4b17a4244f0c8237701cf323f177
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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