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Acetic Acid → 4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-one

HRID 1096242
ノート
印刷プレビュー

反応式

HRID 1096242 の反応式
Cl.[CH2:2]1[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][C@H:5]2[OH:10])[CH2:3]1.CCN(CC)CC.CC(O)=O.C(OC([N:29]1[CH2:35][CH2:34][C:33](=[O:36])[N:32]([CH2:37][CH2:38][CH:39]=O)[CH2:31][CH2:30]1)=O)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:10][C@@H:5]1[CH2:6][N:7]([CH2:39][CH2:38][CH2:37][N:32]2[C:33](=[O:36])[CH2:34][CH2:35][NH:29][CH2:30][CH2:31]2)[CH2:8][CH2:9][C:4]21[CH2:3][CH2:2]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2 回HCID 866158685-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

生成物 1

HCID 66783235
4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-one
収率 71.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2) 0.16 g (1 mmol) in CH2Cl2 (5 ml) was added Et3N 0.14 ml (1 mmol) and AcOH 0.11 ml (2 mmol) followed by a solution of 5-oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester 0.34 g (1 mmol) in CH2Cl2 (5 ml) and finally sodium triacetoxyborohydride 0.25 g (1 mmol). The mixture was stirred for 1 h after which time sat. aq. NaHCO3. solution was added, the reaction extracted with in CH2Cl2, dried (Na2SO4) and concentrated. The residue was taken up in 1 M HCl solution in dioxane (10 ml), stirred for 10 minutes before the solvent was evaporated. The residue was then dissolved in sat. aq. NaHCO3. solution the water removed by evaporation, and the solid extracted with CH2Cl2:MeOH (9:1). Concentration afforded the title compound 0.2 g (71%) as yellow oil. MS: 282.1 (MH+).

後処理

  1. additionsolution was added
  2. extractionthe reaction extracted with in CH2Cl2
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customwas evaporated
  6. dissolutionThe residue was then dissolved in sat. aq. NaHCO3
  7. customsolution the water removed by evaporation
  8. extractionthe solid extracted with CH2Cl2:MeOH (9:1)
  9. concentrationConcentration

出典と根拠

ORDレコード
ord-602058d10fad49f8a2294a952cf19aea
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08138175B2

反応ノート

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