1,2-Dichloroethane → Tert-butyl 6,8-dioxo-5-azaspiro[3.5]nonane-5-carboxylate

HRID 1175121ノート

反応式

HRID 1175121 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:13][C:14]([OH:16])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH3:21][C:22]1(C)OC(=O)CC(=O)[O:23]1.Cl.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:22](=[O:23])[CH2:21][C:14](=[O:16])[CH2:13][C:9]21[CH2:10][CH2:11][CH2:12]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 10751878(1-Aminocyclobut-1-yl)acetic acid, N-BOC protectedHCID 21885828Hydrate;hydrochloride

生成物 1

HCID 59558334Tert-butyl 6,8-dioxo-5-azaspiro[3.5]nonane-5-carboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(1-tert-Butoxycarbonylamino-cyclobutyl)-acetic acid (6 g; 26 mmol) (Eur.J.Med.Chem. 34 (1999) 363), EDC (7.5 g; 39 mmol) DMAP (4.8 g; 39 mmol) and Meldrum's acid (3.77 g; 26 mmol) in CH2Cl2 (120 ml) are stirred at room temperature over night and poured on 2N HCl/water (40 ml/400 ml). The aqueous phase is extracted with CH2Cl2 twice, the organic phases are combined and dried over Na2SO4 and evaporated to dryness. The orange-colored residue is taken up in ethyl acetate (200 ml) and refluxed for 2.5 hours, diluted with hexanes (600 ml) and purified via chromatography (SiO2; Hexanes/acetone 92:8) yielding the title compound as yellowish crystals in a modest purity, which is sufficient to perform the next steps.

後処理

  1. extractionThe aqueous phase is extracted with CH2Cl2 twice
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. temperaturerefluxed for 2.5 hours
  5. additiondiluted with hexanes (600 ml)
  6. custompurified via chromatography (SiO2; Hexanes/acetone 92:8)

出典と根拠

ORDレコード
ord-ccfcf49d365942e0be98591af4459599
出典データセット
uspto-grants-2010_11
特許番号
US07838674B2

反応ノート

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