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

HRID 2243190Notes

Reaction equation

HRID 2243190 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.[C@@H:22]([NH2:26])([CH2:24][CH3:25])[CH3:23]>O1CCCC1.C(OCC)(=O)C>[CH:22]([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])[CH3:23]

Participants

5

Reactant 2

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

Product 1

HCID 68508938HCID 68508938, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution comprised of (±)-4-(4,4-dimethyl-2-oxo-tetrahydro-furan-3-yloxy)-2-trifluoromethyl-benzonitrile (1.345 g; 4.495 mmol) in tetrahydrofuran (5 mL) at ambient temperature under a nitrogen atmosphere is added (S)-(+)-sec-butylamine (0.4931 g; 6.742 mmol.) The reaction mixture is stirred for eight days. The reaction mixture is diluted with ethyl acetate and washed with 1N aqueous hydrochloric acid and with a brine solution. The organic phase is dried over anhydrous magnesium sulfate and is concentrated in vacuo to afford 1.633 of a white solid as a mixture of diastereomers; HPLC UV purity: 94% (two diastereomers.)

Workup

  1. washwashed with 1N aqueous hydrochloric acid and with a brine solution
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. concentrationis concentrated in vacuo
  4. customto afford 1.633 of a white solid
  5. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-1eccedb24211484b8b864f060459df6c
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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