Water → 3-(1-hydroxyethyl)-4-(morpholinomethyl)-1H-isochromen-1-one

HRID 634381Notes

Reaction equation

HRID 634381 reaction equation
[Si]([O:8][CH:9]([C:11]1[O:12][C:13](=[O:28])[C:14]2[C:19]([C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[OH:8][CH:9]([C:11]1[O:12][C:13](=[O:28])[C:14]2[C:19]([C:20]=1[CH2:21][N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 1238137353-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one

Product 1

HCID 1181311663-(1-hydroxyethyl)-4-(morpholinomethyl)-1H-isochromen-1-oneYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one (Intermediate B59.3, 0.203 g, 0.503 mmol) was dissolved in THF (7 mL); TBAF (1.0 M solution in THF, 0.33 ml, 0.33 mmol) was added drop-wise and the resulting mixture was stirred at room temperature for 2 hrs. Water (10 ml) was added and the mixture was extracted twice with DCM; the combined organic layers were dried over sodium sulfate and evaporated to dryness. The crude was purified by reverse phase flash chromatography on C18 Biotage cartridge ((H2O:CH3CN=95:5 to 80:20, with 0.1% HCOOH) to afford the title compound (0.145 g). The product was used in the next step without further purifications.

Workup

  1. extractionthe mixture was extracted twice with DCM
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude was purified by reverse phase flash chromatography on C18 Biotage cartridge ((H2O:CH3CN=95:5 to 80:20, with 0.1% HCOOH)

Sources & evidence

ORD record
ord-35ef3bcc5b6c4c9a84fd20bbc149a0e7
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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