Sodium Cyanide → HCID 45087749、化合物

HRID 497072ノート

反応式

HRID 497072 の反応式
[C-:1]#[N:2].[K+].[C-]#N.[Na+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:26][C@H:27]1[N:31]([CH3:32])[C:30](=[O:33])[CH2:29][CH2:28]1>CC#N>[CH3:32][N:31]1[C:30](=[O:33])[CH2:29][CH2:28][C@H:27]1[CH2:26][C:1]#[N:2]

参加物

6

反応物 4

HCID 8929Sodium CyanideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 69528544479411-59-1

生成物 1

HCID 45087749HCID 45087749、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

KCN (886 mg, 13.6 mmols), NaCN (666 mg, 13.6 mmols) and 18-crown-6 (207 mg, 1.02 mmols) were added to a CH3CN (25 ml) solution of the (5S)-5-(bromomethyl)-1-methylpyrrolidin-2-one (1.31 g, 6.8 mmols), and the mixture was heated for 43 hours under reflux. The inorganic matter was filtered off, and the filtrate was diluted with AcOEt (50 ml). The dilution was washed with a saturated solution (30 ml) of NaCl, and dried over MgSO4. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 50 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2S)-1-methyl-5-oxopyrrolidin-2-yl)ethanenitrile as a mixture (1.05 g) with impurities difficult to separate: IR νmax (film) cm−1: 2246, 1685. 1H-NMR (CDCl3)δ: 3.85-3.76 (1H, m), 2.88 (3H, s), 2.68 (1H, dd, J=17.0, 4.4 Hz), 2.61 (1H, dd, J=17.0, 6.0 Hz), 2.62-2.48 (1H, m), 2.46-2.30 (2H, m), 2.00-1.86 (1H, m). MS m/z: 138 (M+), 98 (100%). HRMS: Calcd. for C7H10N2O: 138.0793 (M+). Found: 138.0794 (M+).

後処理

  1. temperaturethe mixture was heated for 43 hours
  2. temperatureunder reflux
  3. filtrationThe inorganic matter was filtered off
  4. additionthe filtrate was diluted with AcOEt (50 ml)
  5. washThe dilution was washed with a saturated solution (30 ml) of NaCl
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-4e3939a3260d420fb634237546827821
出典データセット
uspto-grants-2005_09
特許番号
US06949553B2

反応ノート

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