Sodium Bicarbonate → Tert-butyl[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamate

HRID 1376017ノート

反応式

HRID 1376017 の反応式
C(=O)(O)[O-].[Na+].[C:6]([O:10][C:11](=[O:31])[NH:12][CH2:13][CH2:14][N:15]1[CH2:22][CH:21]2[O:23][CH:17]([CH2:18][N:19](CC3C=CC=CC=3)[CH2:20]2)[CH2:16]1)([CH3:9])([CH3:8])[CH3:7]>C(O)C.ClCCl.[Pd]>[C:6]([O:10][C:11](=[O:31])[NH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH:17]2[O:23][CH:21]([CH2:20][NH:19][CH2:18]2)[CH2:22]1)([CH3:9])([CH3:7])[CH3:8]

参加物

6

反応物 2

HCID 516892Sodium BicarbonateHCID 10144351[2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester

生成物 1

HCID 9970422Tert-butyl[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamate収率 89.1%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Sodium bicarbonate (0.058 g, 0.069 mmol) and 5% Pd/C (0.250 g, Johnson Matthey Type 440 paste) were added to a solution of [2-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester (see Example I (Alternative I) above; 1 g, 2.77 mmol) in ethanol (10 mL). The mixture was then hydrogenated at 500 kPa (5 bar) for 18 hours. The reaction mixture was filtered through Celite® and then washed with ethanol (20 mL). The solution was concentrated under reduced pressure to give an oil. This was dissolved in dichloromethane (20 mL) and washed with sodium hydroxide (1 M, 10 mL). The organic phase was separated, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give the title compound as a yellow solid (0.67 g, 87%).

後処理

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashed with ethanol (20 mL)
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil
  5. washwashed with sodium hydroxide (1 M, 10 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-e838648c0729424aa720dbf942f06dc0
出典データセット
uspto-grants-2007_01
特許番号
US07169921B2

反応ノート

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