Ammonium Chloride → 4-(2-Bromophenyl)-3-cyano-N-benzylpyrrolidine

HRID 1859051Notes

Reaction equation

HRID 1859051 reaction equation
[CH2:1]([N:8]([CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])Cl)[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl-].[NH4+]>O1CCCC1>[Br:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:14]1[CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH:10]1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 221232083-{Benzyl-[2-(2-bromophenyl)-2-chloroethyl]amino}propanenitrile

Product 1

HCID 221232224-(2-Bromophenyl)-3-cyano-N-benzylpyrrolidineYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

The 90.2 g of product obtained in Step 3 are dissolved in tetrahydrofuran. The solution is cooled to -70° C. and 143 ml of a 2M solution of sodium hexamethyldisilazide are poured in dropwise. After 1 hour at -70° C. and then 12 hours at ambient temperature, the reaction mixture is poured into 300 ml of saturated aqueous ammonium chloride solution and then extracted with ether. The combined organic phases are washed and dried. After evaporating, 78.5 g of expected product are obtained in the form of a mixture of diastereoisomers.

Workup

  1. extractionextracted with ether
  2. washThe combined organic phases are washed
  3. customdried
  4. customAfter evaporating

Sources & evidence

ORD record
ord-325ea73bcad54a0cabe026132d93e27a
Source dataset
uspto-grants-2000_11
Patent number
US06153640

Reaction notes

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