Water → Methyl [4-cyano-1-(trifluoroacetyl)-2,3-dihydro-1h-1-benzazepin-2-yl]acetate

HRID 1761028Notes

Reaction equation

HRID 1761028 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH2:7][CH:6]1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:4].[Li][C:32]#[N:33].C1OCCOCCOCCOC1.O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:32]([C:8]1[CH2:7][CH:6]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[N:5]([C:3](=[O:4])[C:2]([F:29])([F:1])[F:30])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=1)#[N:33]

Participants

7

Reactant 4

HCID 962WaterHCID 92691,4,7,10-TetraoxacyclododecaneHCID 91577583Methyl (1-(trifluoroacetyl)-4-{[(trifluoromethyl)sulphonyl]oxy}-2,3-dihydro-1h-1-benzazepin-2-yl)acetateHCID 178506913HCID 178506913, compound

Product 1

HCID 91539061Methyl [4-cyano-1-(trifluoroacetyl)-2,3-dihydro-1h-1-benzazepin-2-yl]acetate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of the compound obtained in Step e (1.35 g; 293 mmol) in 16 ml of anhydrous toluene is added to a mixture of LiCN (0.5 M in DMF) (11.72 ml; 5.86 mmol), (Ph3P)4Pd (237 mg; 0.205 mmol) and 12-crown-4 (36 mg; 0.205 mmol) under an argon. atmosphere. The reaction mixture is stirred at ambient temperature for 6 hours. Water (10 ml) is added to the reaction mixture, and the organic phase is extracted with diethyl ether. After drying and concentration, the residue obtained is purified on silica gel (eluant:heptane/EtOAc) to yield the title product.

Workup

  1. extractionthe organic phase is extracted with diethyl ether
  2. customAfter drying
  3. concentrationconcentration
  4. customthe residue obtained
  5. customis purified on silica gel (eluant:heptane/EtOAc)

Sources & evidence

ORD record
ord-509b45decb944185882a990907552a84
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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