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Ethylamine → 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-N-ethyl-7-fluorobenzo[d]isoxazole-3-carboxamide

HRID 245457
Notes
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Reaction equation

HRID 245457 reaction equation
C[Al](C)C.[CH2:5]([NH2:7])[CH3:6].[Si:8]([O:25][CH2:26][C:27]1[C:28]([N:42]2[CH2:47][C@H:46]([CH3:48])[O:45][C@H:44]([CH3:49])[CH2:43]2)=[C:29]([F:41])[C:30]2[O:34][N:33]=[C:32]([C:35](OCC)=[O:36])[C:31]=2[CH:40]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Si:8]([O:25][CH2:26][C:27]1[C:28]([N:42]2[CH2:43][C@H:44]([CH3:49])[O:45][C@H:46]([CH3:48])[CH2:47]2)=[C:29]([F:41])[C:30]2[O:34][N:33]=[C:32]([C:35]([NH:7][CH2:5][CH3:6])=[O:36])[C:31]=2[CH:40]=1)([C:21]([CH3:22])([CH3:24])[CH3:23])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6341EthylamineHCID 16682925TrimethylaluminumHCID 67357675ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carboxylate2×

Product 1

HCID 673575425-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-N-ethyl-7-fluorobenzo[d]isoxazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
2×

Procedure

Under a nitrogen atmosphere, trimethylaluminum (2M in toluene, 1206 μl, 2.41 mmol) was slowly added (gas evolution) to an ice cooled solution of ethylamine (2M in THF) (1206 μl, 2.41 mmol) in 7 ml of toluene. The reaction was allowed to warm to room temperature and stirred for 2 hours. Ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carboxylate, (Intermediate 204, 190 mg, 0.32 mmol) was added as a solution in toluene (3 ml). The reaction was stirred at 45° C. for 18 hours. The reaction was quenched drop wise (vigorous gas evolution) with 2 ml of 1N HCl. The crude reaction was filtered to remove solids, diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed twice with brine, dried over MgSO4 and concentrated to give an oil. The oil was purified by silica gel column chromatorgraphy using a gradient of hexanes to ethyl acetate. Fractions were combined and concentrated to give the title compound. (170 mg, 0.288 mmol, 90%).

Workup

  1. stirringThe reaction was stirred at 45° C. for 18 hours
  2. customThe reaction was quenched drop wise (vigorous gas evolution) with 2 ml of 1N HCl
  3. customThe crude reaction
  4. filtrationwas filtered
  5. customto remove solids
  6. additiondiluted with water
  7. extractionextracted twice with ethyl acetate
  8. washwashed twice with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customto give an oil
  12. customThe oil was purified by silica gel column chromatorgraphy
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-40dbd40fe20c4ad6b7f12c3d7cc0f27d
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes