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

HRID 2107978
Notes
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Reaction equation

HRID 2107978 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 176
Acetic Acid
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 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-2cf242dabfb54d2fbef5551dd97448f7
Source dataset
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04937235

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes