Triethylamine → HCID 59293487, compound

HRID 883271Notes

Reaction equation

HRID 883271 reaction equation
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH3:16][N:17]([CH3:29])[C@@H:18]1[CH2:27][CH2:26][C:25]2[C:24](O)=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:19]1.CCN(CC)CC>C(Cl)Cl.[Cl-].[Na+].O>[F:6][C:5]([F:8])([F:7])[S:2]([O:1][C:24]1[C:25]2[CH2:26][CH2:27][C@@H:18]([N:17]([CH3:29])[CH3:16])[CH2:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 59293500HCID 59293500, compound

Product 1

HCID 59293487HCID 59293487, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tf2O (4.3 mL, 25.452 mmol) was dropwise added to a −78° C. cooled solution of (6R)-6-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-ol (4.25 g, 22.218 mmol) and Et3N (8.0 mL, 57.396 mmol) in CH2Cl2 (90 mL). The reaction was completed after 5 min at low temperature. The reaction mixture was poured into brine (200 mL) and extracted with CH2Cl2 (2×200 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (5-10% MeOH/CH2Cl2) to furnish 5.10 g of the title product (Rf=0.4 (10% MeOH/CH2Cl2), pale brown colored oil, 71% yield).

Workup

  1. extractionextracted with CH2Cl2 (2×200 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel (5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4723d9b5ba154015bb994ed7a53897f0
Source dataset
uspto-grants-2012_08
Patent number
US08236845B2

Reaction notes

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