Triethylamine → HCID 22876525, compound

HRID 1003647Notes

Reaction equation

HRID 1003647 reaction equation
C(N(CC)CC)C.[NH2:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@H:11]([C:12]2([CH3:17])[CH3:16])[C@@H:10]1[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl>[S:27]([NH:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@H:11]([C:12]2([CH3:17])[CH3:16])[C@@H:10]1[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)([CH3:30])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14352646HCID 14352646, compound

Product 1

HCID 22876525HCID 22876525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.9 ml) was added to a solution of (1S,2S,3S,5R)-3-amino-2-[2-(2-tetrahydropyranyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]heptane (3.25 g) in methylene chloride (30 ml). The reaction solution was cooled. To the above solution, mesyl chloride (1.0 ml) was dropped slowly. The reaction solution was allowed to stand for 1 hour. The reaction solution was extracted with methylene chloride. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (3.05 g) having the following physical data.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionThe reaction solution was extracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8e7bc16dfbe24b8bacbef4881e434638
Source dataset
uspto-grants-2000_04
Patent number
US06046236

Reaction notes

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