Acetic Acid → HCID 23506111, compound

HRID 1017042Notes

Reaction equation

HRID 1017042 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6].[F:10][C:11]([F:24])([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O)[CH:12]([F:14])[F:13].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[F:10][C:11]([F:24])([O:15][C:16]1[CH:17]=[C:18]([CH2:19][NH:1][CH2:2][CH2:3][CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6])[CH:21]=[CH:22][CH:23]=1)[CH:12]([F:13])[F:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 5049666Sodium triacetoxyborohydrideHCID 112058104-Amino-2-hydroxy-1,1,1-trifluorobutane

Product 1

HCID 23506111HCID 23506111, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

EX-666A) The 4amino-2-hydroxy-1,1,1-trifluorobutane (1.0 g, 7.0 mmol) from EX-611A and 3-(1,1,2,2-tetrafluoroethoxy)benzaldehyde (1.5 g, 7.0 mmol) were dissolved in 20 mL of dichloroethane and acetic acid (0.40 mL, 7.7 mmol), then solid NaBH(OAc)3 (1.8 g, 8.4 mmol) was added. The mixture was stirred at room temperature for 3 d, then quenched with water and extracted with ether. The ether layer was washed with water and brine, then dried over MgSO4, and evaporated to give 1.6 g of crude product, which was purified by reverse phase HPLC to give 0.90 g (37%) of the desired 4-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1,-trifluoro-2-butanol product as a yellow oil. HRMS calcd. for C13H14F7NO2: 350.0991 [M+H]+, found: 350.0971.

Workup

  1. customquenched with water
  2. extractionextracted with ether
  3. washThe ether layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give 1.6 g of crude product, which
  7. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-7a45730790704537af44c23b5ca43903
Source dataset
uspto-grants-2002_11
Patent number
US06476057B1

Reaction notes

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