Tetrabutylammonium Fluoride → HCID 90295766, compound

HRID 1050199Notes

Reaction equation

HRID 1050199 reaction equation
[O:1]([CH2:9][C@H:10]1[C@H:18]2[N:13]([C:14]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C:24]4=[O:29])=[CH:19][C:15]=3[O:16][CH2:17]2)[C:12](=[O:30])[O:11]1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.CO>C1COCC1>[OH:1][CH2:9][C@H:10]1[C@H:18]2[N:13]([C:14]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C:24]4=[O:29])=[CH:19][C:15]=3[O:16][CH2:17]2)[C:12](=[O:30])[O:11]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226129Dichloromethane methanolHCID 90295765HCID 90295765, compound2×

Product 1

HCID 90295766HCID 90295766, compoundYield 70.86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound (3R,3aS)-3-((t-butyldimethylsiloxy)methyl)-7-(3-oxomorpholin-4-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1 (3H)-one (3.6 g, 8.295 mmol) prepared as above in (a) was dissolved in 50 ml of THF, cooled to 0° C., to which was slowly added tetra-n-butylammonium fluoride (1M, 10 ml). The resulting mixture was raised to room temperature and reacted for 2 h. TLC (DCM/MeOH=10/1) was employed to monitor the reaction. After the reaction completed, THF was evaporated. The resulting mixture was washed with ethyl acetate/n-hexane=1/1 under stirring, filtered under reduced pressure, and dried to afford 1.88 g of white solid, yield 70.86%.

Workup

  1. temperatureThe resulting mixture was raised to room temperature
  2. customreacted for 2 h
  3. customthe reaction
  4. customTHF was evaporated
  5. washThe resulting mixture was washed with ethyl acetate/n-hexane=1/1
  6. filtrationfiltered under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-cde2caa5f11c42bd9c284de19cbb4fee
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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