Sodium Cyanide → HCID 45087749, 화합물

HRID 497072노트

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HRID 497072 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 45087749HCID 45087749, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-4e3939a3260d420fb634237546827821
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949553B2

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