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Methanol → 2-Amino-4,4,4-trifluorobutan-1-ol

HRID 1486255
Notes
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Reaction equation

HRID 1486255 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.Cl.[NH2:9][CH:10]([CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](O)=[O:12].CO>C1COCC1>[NH2:9][CH:10]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:11][OH:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 27565662-Amino-4,4,4-trifluorobutanoic acid hydrochlorideHCID 4148881Lithium borohydride

Product 1

HCID 534164332-Amino-4,4,4-trifluorobutan-1-ol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

12.9 ml of 2 M of lithium borohydride solution in THF (25.8 mmol, 2.5 equivalents) were initially charged in 20 ml of THF, 6.5 ml of chlorotrimethylsilane (51.1 mmol, 5 equivalents) were added and the mixture was stirred at RT for 5 min. Then 2.0 g of rac-2-amino-4,4,4-trifluorobutanoic acid hydrochloride (10.3 mmol, 1 equivalent) were added in portions and the mixture was stirred at room temperature overnight. Then 20.4 ml of methanol were added dropwise and, on completion of addition, the mixture was concentrated. The residue was admixed with 12 ml of a 20% aqueous potassium hydroxide solution and extracted three times with dichloromethane. The combined organic solutions were dried over sodium sulphate, filtered and concentrated. 1.58 g (96% of theory; 90% purity) of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationthe mixture was concentrated
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic solutions were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-208b4667cd34443eb882545ae298d99a
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422285B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes