Trifluoroacetic acid → ethyl P-(4-amino-1,1,1-trifluoro-but-2-yl)-P-methyl-phosphinate trifluoroacetate

HRID 865855Notes

Reaction equation

HRID 865855 reaction equation
[C:1]([CH2:3][CH:4]([P:9]([CH3:14])(=[O:13])[O:10][CH2:11][CH3:12])[C:5]([F:8])([F:7])[F:6])#[N:2].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18]>[Pt]=O>[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[NH2:2][CH2:1][CH2:3][CH:4]([P:9]([CH3:14])(=[O:13])[O:10][CH2:11][CH3:12])[C:5]([F:8])([F:6])[F:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10421332ethyl P-(3-cyano-1,1,1-trifluoro-prop-2-yl)-P-methyl-phosphinate

Product 1

HCID 23374758ethyl P-(4-amino-1,1,1-trifluoro-but-2-yl)-P-methyl-phosphinate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

250 mg of platinum oxide are added to a solution of 458.28 mg (2 mmol) of ethyl P-(3-cyano-1,1,1-trifluoro-prop-2-yl)-P-methyl-phosphinate dissolved in 28 ml of trifluoroacetic acid, and the resulting mixture is hydrogenated at 25° and 4 bar. The catalyst is filtered off and the filtrate is evaporated to dryness under reduced pressure. The resulting crude product is chromatographed on 70 g of Opti-Up® C12 with acetonitrile as the eluent. The product-containing fractions are combined and evaporated under reduced pressure to give ethyl P-(4-amino-1,1,1-trifluoro-but-2-yl)-P-methyl-phosphinate trifluoroacetate as an oil.

Workup

  1. customis hydrogenated at 25°
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. customThe resulting crude product is chromatographed on 70 g of Opti-Up® C12 with acetonitrile as the eluent
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fa9223cf6e404efb9fac9941bcbd2fa2
Source dataset
uspto-grants-1996_10
Patent number
US05567840

Reaction notes

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