Ethyl benzoylformate → HCID 178472739, compound

HRID 853126Notes

Reaction equation

HRID 853126 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH2:4][CH2:3]1.[CH2:18]([O:20][C:21](=[O:30])[C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:19].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CCO.CCOCC>[CH2:18]([O:20][C:21](=[O:30])[CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([C:8]([OH:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])[CH2:6][CH2:7]1)[CH3:19].[CH2:18]([O:20][C:21](=[O:30])[CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([OH:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])[CH2:6][CH2:7]1)[CH3:19]

Participants

8

Reactant 4

HCID 15349Ethyl benzoylformateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86605616HCID 86605616, compound

Product 2

HCID 178472739HCID 178472739, compoundYield 25%HCID 178472740HCID 178472740, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 300 mg (1.0 mmol) of the acetate salt of 2-(4-amino-cyclohexyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 2.1) in 5 mL of EtOH was treated with 227 mg (1.0 mmol) of oxo-phenyl-acetic acid ethyl ester and with 87 mg (1.0 mmol) of sodium cyanoborohydride. The mixture was stirred overnight at RT and distributed between a saturated aqueous solution of NaHCO3 and Et2O. Drying of the combined organic phases over Na2SO4 and chromatography on silica gel with heptane/EtOAc 4:1 yielded ca. 100 mg (25%) of cis phenyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexylamino]-acetic acid ethyl ester and ca. 100 mg (25%) of trans phenyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexylamino]-acetic acid ethyl ester as a colorless oil, MS: 428 (M+H)+.

Workup

  1. dry with materialDrying of the combined organic phases over Na2SO4 and chromatography on silica gel with heptane/EtOAc 4:1

Sources & evidence

ORD record
ord-a07e49fcbbdd42eabdfc9e74e273083a
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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