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

HRID 1012018노트

반응식

HRID 1012018 반응식
[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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ebf22027614840a7862850e9751d0736
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

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