Ethylenediamine → 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-enoic acid methyl ester

HRID 2052925노트

반응식

HRID 2052925 반응식
[BH4-].[Na+].C(N)CN.[CH3:7][O:8][C:9](=[O:25])[CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][N:16]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C@@H:17]1[CH2:23][OH:24].[H][H]>C(O)C.[Ni](Cl)Cl>[CH3:7][O:8][C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH:13]=[CH:14][CH2:15][N:16]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C@@H:17]1[CH2:23][OH:24]

참가 물질

7

반응물 4

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 690212337-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 690228967-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-enoic acid methyl ester수율 38.8%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 702Ethanol용매2회

실험 절차

95% Ethanol (0.5 mL) was added to a mixture of nickel (II) chloride (105 mg, 0.81 mmol) and sodium borohydride (15 mg, 0.40 mmol). The mixture immediately turned black. After 15 min at rt, ethylene diamine (86 μL, 1.29 mmol) was added. After 15 min at rt, a solution of 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (from Example 1, step 3, 43.3 mg, 0.16 mmol) in 95% ethanol (1.0 mL) was added via cannula. A hydrogen atmosphere was established by evacuating and refilling with hydrogen (3×) and the reaction mixture was stirred under a balloon of hydrogen for 19 h. The reaction mixture was filtered through celite, washing with ethanol, and the filtrate was concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 16.7 mg (38%) of 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-enoic acid methyl ester.

후처리

  1. waitAfter 15 min at rt
  2. customby evacuating
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashing with ethanol
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)

출처 및 근거

ORD 기록
ord-8e2f6e94895e4ab49118871f4f4ac8d1
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326716B2

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