Hydrochloric Acid → N-((3R,5S)-5-Hydroxymethyl-pyrrolidin-3-yl)-acetamide hydrochloride

HRID 1012018ノート

反応式

HRID 1012018 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].CO[C:9]([C@@H:11]1[CH2:15][C@@H:14]([N:16]=[N+]=[N-])[CH2:13][N:12]1C(OC(C)(C)C)=O)=[O:10].C(=O)([O-])[O-].[Na+].[Na+].[C:32](OC(=O)C)(=[O:34])[CH3:33].[ClH:39]>C1COCC1.O1CCOCC1.O>[ClH:39].[OH:10][CH2:9][C@H:11]1[NH:12][CH2:13][C@H:14]([NH:16][C:32](=[O:34])[CH3:33])[CH2:15]1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 11369242(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl EsterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 66901605N-((3R,5S)-5-Hydroxymethyl-pyrrolidin-3-yl)-acetamide hydrochloride収率 80%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To an ice-cold suspension of lithium aluminium hydride (0.6 g, 15 mmol) in THF (10 ml) was added a solution of (2S,4R)-4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.0 g, 4 mmol) in THF (5 mL) and the mixture stirred for 1 h. Water was then cautiously added to the reaction and the mixture filtered and concentrated. The residue was then taken up in CH2Cl2 (10 ml) and saturated sodium carbonate (10 ml) and acetic anhydride (0.3 ml, 3 mmol) added. The mixture was stirred for 2 h after which time the organic was collected, dried (Na2SO4) and concentrated. The residue (0.6 g, 2 mmol) was then treated with 4 M hydrochloric acid in dioxane (5 ml) for 1 h, evaporation of the solvent afforded the title compound (0.5 g, 80%) as a yellow solid. MS: 159.1 (MH+).

後処理

  1. filtrationthe mixture filtered
  2. concentrationconcentrated
  3. stirringThe mixture was stirred for 2 h after which time the
  4. customorganic was collected
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customevaporation of the solvent

出典と根拠

ORDレコード
ord-ebf22027614840a7862850e9751d0736
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

反応ノート

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