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Trifluoroacetic acid → a-(RS)-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetate

HRID 362133
Notes
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Reaction equation

HRID 362133 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].Cl[CH:12]([B:15]1[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]1)[CH2:13][CH3:14].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>O1CCCC1>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[CH2:13]([CH:12]([B:15]1[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]1)[NH2:5])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2733832Lithium hexamethyldisilazaneHCID 193646402-(1-Chloropropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 19364709a-(RS)-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetateYield 16.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

10 ml (10 mmol) of 1M lithium bis(trimethylsilyl)amide in tetrahydrofuran were added dropwise to a solution of 2.03 g (9.9 mmol) of 2-[1(RS)-chloropropyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in 20 ml tetrahydrofuran under a nitrogen atmosphere at -78° C. The solutionwas then stirred overnight at room temperature. The solvent was removed by evaporation and the residue was taken up in diethyl ether. Insoluble material was removed by filtration and the filtrate was cooled to 0° C. 2.3 ml (30 mmol) of trifluoroacetic acid were added and the solution was stirred at 0° C. for 30 minutes. The resulting precipitate was filtered off and dried to give 0.5 g of α-(RS)-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetate as a white solid.

Workup

  1. customThe solvent was removed by evaporation
  2. customInsoluble material was removed by filtration
  3. temperaturethe filtrate was cooled to 0° C
  4. stirringthe solution was stirred at 0° C. for 30 minutes
  5. filtrationThe resulting precipitate was filtered off
  6. customdried

Sources & evidence

ORD record
ord-4135558e45b94831b48bf4ed2b1d5b41
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05866684

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes