Borane;tetrahydrofuran → HCID 11683624, compound

HRID 854486Notes

Reaction equation

HRID 854486 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[N:18]([CH2:29][CH3:30])[C:19](=O)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:15])([F:16])[F:14])[CH:5]=[CH:4][C:3]=1[N:18]([CH2:29][CH3:30])[CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86602509HCID 86602509, compound

Product 1

HCID 11683624HCID 11683624, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 70 mg (0.15 mmol) of N-[2-chloro-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-N-ethyl-3-phenyl-propionamide in 3 mL of THF was treated with 1 mL of 1M BH3THF-complex in THF and stirred for 10 hours at 80° C. in a sealed tube. Evaporation of the solvent and column chromatography on silica gel with CH2Cl2/n-heptane 1:1 yielded 60 mg (91%) of 2-{3-chloro-4-[ethyl-(3-phenyl-propyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, colorless oil, MS: 440 (MH+, 1Cl).

Workup

  1. customEvaporation of the solvent and column chromatography on silica gel with CH2Cl2/n-heptane 1:1

Sources & evidence

ORD record
ord-db0dd3b8806e430b9fd963b52a4a6bb6
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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