Sodium Bicarbonate → Methyl 2,2-dimethyl-3-[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoate

HRID 733087

반응식

HRID 733087 반응식
[O:1]=[C:2]1[C:10]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:16].[CH3:25][C:26]([CH3:33])([CH:31]=O)[C:27]([O:29][CH3:30])=[O:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:25][C:26]([CH3:33])([CH2:31][N:22]1[CH2:21][CH2:20][CH:19]([CH2:18][NH:17][C:15]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([CH2:14][CH2:13][CH2:12][CH2:11]3)[C:2]2=[O:1])=[O:16])[CH2:24][CH2:23]1)[C:27]([O:29][CH3:30])=[O:28]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11137194Methyl 2,2-dimethyl-3-oxopropanoateHCID 672325932'-Oxo-N-(piperidin-4-ylmethyl)spiro[cyclopentane-1,3'-indole]-1'(2'H)-carboxamide

생성물 1

HCID 67232986Methyl 2,2-dimethyl-3-[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoate수율 23%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2′-oxo-N-(piperidin-4-ylmethyl)spiro[cyclopentane-1,3′-indole]-1′(2′H)-carboxamide (480 mg, 1.5 mmol, step 2 of Example 2) and methyl 2,2-dimethyl-3-oxopropanoate (248 mg, 1.7 mmol, Kim, Hwa-Ok et al., Synth. Commun., 1997, 27, 2505) in CH2Cl2 (40 mL) was added sodium triacetoxyborohydride (623 mg, 2.9 mmol) in one portion at room temperature. The mixture was stirred for 20 h at ambient temperature. To the mixture was added sat. NaHCO3 aq. (10 mL), extracted with CH2Cl2 (30 mL×2), dried over MgSO4, filtered and concentrated gave yellow oil. The residue was chromatographed on a column of aminopropyl-silica gel eluting with hexane/ethyl acetate (9:1) to give 150 mg (23%) of the title compound as clear colorless oil.

후처리

  1. extractionextracted with CH2Cl2 (30 mL×2)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customgave yellow oil
  6. customThe residue was chromatographed on a column of aminopropyl-silica gel eluting with hexane/ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-815dfd564ba744989e3151e9f144adbc
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589109B2

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