1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18646605, compound

HRID 1030653Notes

Reaction equation

HRID 1030653 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11](Cl)[C@@H:10]1[OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].N12CCCN=C1CCCCC2>O1CCCC1.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]2[O:20][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18646599HCID 18646599, compound

Product 1

HCID 18646605HCID 18646605, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-(1R,2R,3R)-3-tert-butoxycarbonylamino-1-chloro-1,2,3,4tetrahydro-2-naphthalenol (348 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (400 mg) in tetrahydrofuran (10 ml) was refluxed for 11/2 hours. The mixture was diluted with methylene chloride, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was recrystallized from cyclohexane (193 mg) to yield the title compound as a white solid, m.p. 118-119° C.

Workup

  1. washwashed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from cyclohexane (193 mg)

Sources & evidence

ORD record
ord-fa7e098acdbd4eb4aac5c1a51b099614
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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