2-Butanamine, (S)- → HCID 68508938, compound

HRID 2243193Notes

Reaction equation

HRID 2243193 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4](=[O:7])[CH:3]1[O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1.[CH3:22][C@H:23]([NH2:26])[CH2:24][CH3:25]>C1COCC1>[CH:23]([NH:26][C:4](=[O:7])[CH:3]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:19])([F:18])[F:20])[CH:10]=1)[C:2]([CH3:21])([CH3:1])[CH2:6][OH:5])([CH2:24][CH3:25])[CH3:22]

Participants

4

Reactant 2

HCID 67137532-Butanamine, (S)-HCID 11695104HCID 11695104, compound

Product 1

HCID 68508938HCID 68508938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-4-(4,4-Dimethyl-2-oxo-tetrahydrofuran-3-yloxy)-2-trifluoromethylbenzonitrile (66.00 g, 221 mmol) was combined with 330 mL dry THF and the (S)-(+)-2-butylamine (total of 64.5 g, 882 mmol), and the reaction mixture was heated at 40-60° C. in a sealed vessel for 124 h. The amber sol'n was concentrated under vac (35-40° C.) to an amber gum. The gum was redissolved in 500 m ethyl acetate “EtOAc” and conc'd again. The gum was redissolved in 500 mL “EtOAc” and passed through a pad of silica. The silica was washed with 500 mL EtOAc and the combined filtrate was concentrated under vac to a pale amber gum.

Workup

  1. concentrationThe amber sol'n was concentrated under vac (35-40° C.) to an amber gum
  2. dissolutionThe gum was redissolved in 500 m ethyl acetate “EtOAc”
  3. dissolutionThe gum was redissolved in 500 mL “EtOAc”
  4. washThe silica was washed with 500 mL EtOAc
  5. concentrationthe combined filtrate was concentrated under vac to a pale amber gum

Sources & evidence

ORD record
ord-ca7dd1fc0b2640afa2d59b36a9cdb7c4
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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