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

HRID 2107995Notes

Reaction equation

HRID 2107995 reaction equation
[CH3:1][C:2]([Si:5]([CH3:17])([CH3:16])[O:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[CH:14])[C:9](=[O:15])[CH2:8]1)([CH3:4])[CH3:3].N1CCCC1.C=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(O)(=O)C.O1CCOCC1>[CH3:4][C:2]([Si:5]([CH3:17])([CH3:16])[O:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[C:14][CH2:30][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:9](=[O:15])[CH2:8]1)([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 31268PyrrolidineHCID 15086816(S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone

Product 1

HCID 15086817(S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.5 g of (S)-4-[[(1,1-dimethylethyl)dimethylsily]oxy]-1-(2-propynyl)-2-pyrrolidinone, 20 ml of dioxane, 0.66 ml of pyrrolidine, 0.32 g of paraformaldehyde, 3.0 ml of acetic acid and 42 mg of cuprous chloride was reacted as described in Example 1 with the substitution of dimethylamine for piperidine. The residue was purified by chromatography (alumina), giving 290 mg of the desired product as a pale yellow oil, [α]D26 =+4° (dichloromethane).

Workup

  1. customwas reacted
  2. customThe residue was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-b0e723e549ce48b7b67c18071f27c71a
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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