Formaldehyde → (S)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-piperidinyl)-2-butynyl]-2-pyrrolidinone

HRID 1710129Notes

Reaction equation

HRID 1710129 reaction equation
[CH3:1][C:2]([Si:5]([CH3:17])([CH3:16])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[C:8]1=[O:15])([CH3:4])[CH3:3].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[CH2:24]=O.[OH-].[NH4+]>O.ClCCl.C(O)(=O)C.O1CCOCC1>[CH3:4][C:2]([Si:5]([CH3:17])([CH3:16])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[C:14][CH2:24][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]1=[O:15])([CH3:1])[CH3:3]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 14923Ammonium HydroxideHCID 15086767HCID 15086767, compound

Product 1

HCID 15086771(S)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-piperidinyl)-2-butynyl]-2-pyrrolidinone

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture 9.7 g of (S)-3-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone, 50 ml of dioxane, 5.7 g of piperidine, 1.8 g of paraformaldehyde, 10.5 ml of acetic acid and 0.16 g of cupric chloride was stirred for 30 minutes and then refluxed for 2 hours. The mixture was cooled in an ice bath, basified with ammonium hydroxide and diluted with water and dichloromethane. The dichloromethane solution was washed with water, dried and concentrated in vacuo, giving the desired product as an oil, [α]D26 =-32° (dichloromethane).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture was cooled in an ice bath
  3. washThe dichloromethane solution was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6abafaa5bcb54cf7a1fc376a8405bdb0
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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