1,1-Dichloroethane → HCID 58808179、化合物

HRID 548941ノート

反応式

HRID 548941 の反応式
[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]

参加物

7

反応物 4

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

生成物 2

HCID 14923Ammonium Hydroxide収率 1%HCID 58808179HCID 58808179、化合物収率 54%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-902bcdbedc3347739f3f0bce9abaae64
出典データセット
uspto-grants-2011_05
特許番号
US07943630B2

反応ノート

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