HCID 11662369, compound → HCID 11639726, compound

HRID 853859Notes

Reaction equation

HRID 853859 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][N:24]=[C:16]3[C:15]3(OCCC[O:27]3)[C:14]=2[CH:13]=1)(=[O:11])=[O:10]>OS(O)(=O)=O>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][C:22]([CH3:25])([CH3:26])[CH2:23][N:24]=[C:16]3[C:15](=[O:27])[C:14]=2[CH:13]=1)(=[O:11])=[O:10]

Participants

3

Reactant 1

HCID 11662369HCID 11662369, compound

Product 1

HCID 11639726HCID 11639726, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

8′-{[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′pyrimido[1,2-a]indole] (0.765 g, 1.70 mmol) was added portion-wise to cold concentrated H2SO4 (10 mL) over a period of 0.5 hr. with cooling in an ice bath. The bath was removed and the reaction stirred at room temp for 1 hr. The reaction mixture was gradually added to ice over a period of 15 min. and was basified to pH 11.1 with concentrated NH4OH keeping the temperature cold by the addition of ice and an external ice bath. The reaction was filtered and the collected solid was dissolved in CH2Cl2, dried over Na2SO4 and concentrated to give the title compound as a bright yellow solid (0.601 g, 90% yield). NMR (400 MHz, DMSO-d6): consistent. IR: consistent. MS: (ES+) m/z 392 [M+H]. Opt. Rot: +74.84 (calculated) in CH2Cl2 (1% concentration) wavelength 589, 25° C.; m.p.: 161-164° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe bath was removed
  3. additionThe reaction mixture was gradually added to ice over a period of 15 min.
  4. additionby the addition of ice and an external ice bath
  5. filtrationThe reaction was filtered
  6. dissolutionthe collected solid was dissolved in CH2Cl2
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e5a9a96a42dc414ebc55dea7b5592442
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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