Triethylamine → 1'-(1,1-Dimethylethyloxycarbonyl)-3-[[[methoxycarbonyl]-methyl]sulfonyl]amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine)

HRID 1902167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902167
[CH3:1][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([NH2:21])[CH2:13]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.Cl[S:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])(=[O:33])=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:3][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:8][CH2:9][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([NH:21][S:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])(=[O:33])=[O:32])[CH2:13]2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 18476131Tert-butyl 3-amino-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Produkt 1

HCID 233677961'-(1,1-Dimethylethyloxycarbonyl)-3-[[[methoxycarbonyl]-methyl]sulfonyl]amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine)

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A sample of 1'-(1,1-dimethylethyloxycarbonyl)-3-amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine), prepared by hydrogenation of 500 mg of oxime (1.58 mmole) as in Example 135, in 2 mL methylene chloride containing 475 mg of DMAP (2.46×1.58 mmole), and 550λ of triethylamine (2.51×1.58 mmole), was stirred under nitrogen in an ice bath while adding a solution of 400λ of 8.4M methyl chlorosulfonylacetate (2.13×1.58 mmole) in 2 mL methylene chloride dropwise over 2-3 minutes. The suspension was stored over night in the refrigerator. It was then washed twice with water, then with 5% citric acid. Atypically, solid material was still present in suspension; this was s removed by filtration, the filtrate dried with magnesium sulfate and concentrated under reduced pressure. Again, solid formed and was removed by filtration. Finally, preparative TLC on four 8"×8"×1,000μ GF silica gel plates using 2:1 ethyl acetate:hexane afforded 389 mg of the title compound

Aufarbeitung

  1. waitThe suspension was stored over night in the refrigerator
  2. washIt was then washed twice with water
  3. customremoved by filtration
  4. dry with materialthe filtrate dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAgain, solid formed
  7. customwas removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0ed3c0458cb440219a05be1984309d36
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05578593

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