Sodium Carbonate → HCID 178513253、化合物

HRID 1051040ノート

反応式

HRID 1051040 の反応式
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[OH:10][C@@H:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH2:13][CH2:12]1>CCO>[OH:3][NH:2][C:20]([C:15]1[C:14]2[CH2:13][CH2:12][C@H:11]([OH:10])[C:19]=2[CH:18]=[CH:17][CH:16]=1)=[NH:21]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 14515308HCID 14515308、化合物

生成物 1

HCID 178513253HCID 178513253、化合物収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To hydroxylamine hydrochloride (0.87 g, 12.5 mmol) and sodium carbonate (1.32 g, 12.5 mmol) in EtOH (20 mL) was added (S)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile INT-2 (1.59 g, 10 mmol) in one portion and the solution was heated to reflux. After 16 h, the reaction was cooled and filtered to remove the solids. The EtOH was removed and the compound purified by chromatography (MeOH/DCM) to give 1.74 g (90%) of (S)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide INT-3 as a white foam. LCMS-ESI (m/z) calculated for C10H12N2O2: 192.1. found: 193.1 [M+H]+, tR=0.56 min. 1H NMR (400 MHz, MeOD) δ 10.30 (s, 1H), 9.97 (s, 1H), 7.72-7.58 (m, 1H), 7.46-7.37 (m, 2H), 5.22 (t, J=6.5, 1H), 3.17-3.03 (m, 1H), 2.99-2.83 (m, 1H), 2.49 (dddd, J=11.4, 8.0, 7.0, 4.4, 1H), 2.02-1.88 (m, 1H). (R)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide is made in an analogous fashion from (R)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile.

後処理

  1. temperaturethe solution was heated to reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. customto remove the solids
  5. customThe EtOH was removed
  6. customthe compound purified by chromatography (MeOH/DCM)

出典と根拠

ORDレコード
ord-8f71c31752df481bba2f835c9c7ba914
出典データセット
uspto-grants-2016_07
特許番号
US09388147B2

反応ノート

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