Formaldehyde → 2,7-Diazaspiro[3.5]nonane-2-carboxylic acid, 7-methyl-, 1,1-dimethylethyl ester

HRID 2066495노트

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HRID 2066495 반응식
Cl.[C:2]([O:6][C:7]([N:9]1[CH2:12][C:11]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].C=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[C:2]([O:6][C:7]([N:9]1[CH2:12][C:11]2([CH2:17][CH2:16][N:15]([CH3:20])[CH2:14][CH2:13]2)[CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 24820549tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

생성물 1

HCID 668709512,7-Diazaspiro[3.5]nonane-2-carboxylic acid, 7-methyl-, 1,1-dimethylethyl ester

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester hydrochloride (100 mg, 0.381 mmol) in DCE (10 mL) was added an aqueous solution of formaldehyde (37% w/w, 40 μL, 0.537 mmol). The mixture was stirred at RT for 10 min, then sodium triacetoxyborohydride (121 mg, 0.571 mmol) was added and stirring was continued for 1 h. Water was added to the reaction mixture before being loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH then eluted with 2 M NH3 in MeOH to give 7-methyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester. To a solution of 7-methyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester in DCM (5 mL) was added TFA (1 mL) and the resulting mixture was stirred at RT for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH to give the title compound as a colourless oil (45 mg, 84%).

후처리

  1. stirringstirring
  2. waitwas continued for 1 h
  3. washThe cartridge was washed with MeOH
  4. washthen eluted with 2 M NH3 in MeOH

출처 및 근거

ORD 기록
ord-6eb26b3965274a04974d029f28b9ff08
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293735B2

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