Acetic Acid → HCID 178439128, compound

HRID 2235301Notes

Reaction equation

HRID 2235301 reaction equation
C(O[C:4](=[O:20])[CH:5]([CH2:17][CH:18]=O)[C:6]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])([CH3:8])[CH3:7])C.[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[C:6]([CH:5]1[CH2:17][CH2:18][N:21]([C@H:22]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]2)[C:4]1=[O:20])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 59299312HCID 59299312, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178439128HCID 178439128, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-(2,4-Dichloro-phenyl)-3-methyl-2-(2-oxo-ethyl)-butyric acid ethyl ester (Preparation 61) in THF and treat with trans-4-Amino-cyclohexan-1-ol (2.0 eq), acetic acid (6.0 eq) and NaBH(OAc)3 (4.0 eq). Allow reaction to stir at room temperature for 17 h and heat to 60° C. for six hours. Cool to room temperature, filter, dilute filtrate with EtOAc, wash with 0.1 N HCl, brine, dry over sodium sulfate and filter. Chromatography (silica, 1:1 to 3:7 hexanes/EtoAc) yields the titled compound in 53% yield: Mass spectrum (API-ES positive) m/z=372.0 (M+H).

Workup

  1. customAllow reaction
  2. temperatureheat to 60° C. for six hours
  3. temperatureCool to room temperature
  4. filtrationfilter
  5. washdilute filtrate with EtOAc, wash with 0.1 N HCl, brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter

Sources & evidence

ORD record
ord-7aa2ca716d8440cd9be60a566aa131d4
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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