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

HRID 1376017노트

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HRID 1376017 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e838648c0729424aa720dbf942f06dc0
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169921B2

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