1,1,1-Trifluoro-N-phenylmethanesulfonamide → 6-Trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester

HRID 48113

Reaktionsgleichung

Reaktionsgleichung von HRID 48113
[CH3:1][C@H:2]([O:9][C:10]([CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH2:13]1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(N[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])C=CC=CC=1>ClCCl.C(N(CC)CC)C>[CH3:1][C@H:2]([O:9][C:10]([CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[CH:18]=2)[CH2:13]1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

5

Edukt 2

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 600724766-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester

Produkt 1

HCID 206321796-Trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution 6-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (1S)-1-methylheptyl ester (37) (1 equi.), and N-phenyl trifluoromethanesulfonamide (1 equi.) in dichloromethane (10 mL/mmole), triethylamine (1.5 equi.) was added at −78 C. The reaction mixture was stirred at that temperature for 1 h and at room temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (1S)-1-methylheptyl ester (45), as a colorless oil (92%).

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7f374d178bd64287acc3ecbfc2555bf1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703082B1

Verknüpfte Notizen

Wird geladen…