4-Bromo-2,2-diphenylbutyronitrile → 3,3-Diphenylpyrrolidine

HRID 2354053Notes

Reaction equation

HRID 2354053 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].Br[CH2:8][CH2:9][C:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]#[N:12]>C1COCC1>[C:13]1([C:10]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9][CH2:8][NH:12][CH2:11]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 4182423,3-Diphenylpyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of LiAlH4 (560 mg, 14.75 mmol) in THF (50 mL) is cooled at 0° C. and a solution of 4-bromo-2,2-diphenylbutyronitrile (1.50 g, 5 mmol) in THF (20 mL) is slowly added. The mixture is stirred at r.t. for 15 h, carefully quenched with MeOH and NaHCO3 and filtered. The filtrate is evaporated, the residue taken up in CH2Cl2 (100 mL) and washed with sat. aq. Na2CO3. (50 mL). The aq. phase is re-extracted with CH2Cl2 (2×50 mL) and the combined organic extracts are dried (Na2SO4), filtered and evaporated. The residue is purified by reversed phase MPLC to provide the title compound.

Workup

  1. customcarefully quenched with MeOH and NaHCO3
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. washwashed with sat. aq. Na2CO3
  5. extractionThe aq. phase is re-extracted with CH2Cl2 (2×50 mL)
  6. dry with materialthe combined organic extracts are dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by reversed phase MPLC

Sources & evidence

ORD record
ord-c97b0b64e6e346ccb7f3ef690ba6cfb9
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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