Tert-Butyl hypochlorite → HCID 86714589, compound

HRID 1025927Notes

Reaction equation

HRID 1025927 reaction equation
[Cl:1][CH2:2][C:3]1([CH3:9])[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[Cl:10]OC(C)(C)C>CO>[Cl:10][N:7]1[C:3]([CH2:2][Cl:1])([CH3:9])[CH2:4][CH2:5][C:6]1=[O:8]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochlorite2×HCID 86714588HCID 86714588, compound

Product 1

HCID 86714589HCID 86714589, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(chloromethyl)-5-methylpyrrolidin-2-one (302 mg, 2.05 mmol) in methanol (20 mL) was cooled in ice water for 10 min, before neat tert-butyl hypochlorite (0.46 mL, 4.1 mmol, 2 equiv.) was added in one portion. Additional tert-butyl hypochlorite (0.46 mL, 4.1 mmol, 2 equiv.) was added after 45 min. After 1 h, the mixture was concentrated in vacuo and the residue absorbed on silica. Chromatography on silica (0-2.5% MeOH/DCM) afforded the N-chloro-pyrrolidinone as a colorless oil (292 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 3.74 (d, J=11.9 Hz, 1H), 3.50 (J=11.9 Hz, 1H), 2.66-2.57 (m, 1H), 2.54-2.40 (m, 2H), 2.10-2.01 (m, 1H), 1.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ171.6 (C), 65.4 (C), 49.1 (CH2), 28.9 (CH2), 27.8 (CH2), 23.1 (CH3); LRMS (ESI/APCI): 182 [M+H]+.

Workup

  1. additionwas added in one portion
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue absorbed on silica

Sources & evidence

ORD record
ord-6b9d457e2eea4229aa7f39a1a7709b2d
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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