1,1-Dichloroethane → HCID 58808179, 화합물

HRID 548941

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HRID 548941 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:20](Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O>[OH-:5].[NH4+:8].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16]([CH3:20])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

생성물 2

HCID 14923Ammonium Hydroxide수율 1%HCID 58808179HCID 58808179, 화합물수율 54%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To an ice cooled solution of 3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (1.55 g, 6 mmol) in dichloroethane (50 mL) formaldehyde (0.68 mL, 9 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxyborohydride (2.54 g, 12 mmol) was added and the reaction stirred at room temperature over night. Aqueous sodium hydrogencarbonate (sat. 50 mL) and water (50 mL) were added and the aqueous phase extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated. Flash chromatography (dichloromethane/methanol 9:1 with 1% ammonium hydroxide) gave 435 mg (27%) 9-methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester.

후처리

  1. stirringthe reaction stirred at room temperature over night
  2. extractionthe aqueous phase extracted five times with dichloromethane
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-902bcdbedc3347739f3f0bce9abaae64
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943630B2

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