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

HRID 1376017Notes

Reaction equation

HRID 1376017 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e838648c0729424aa720dbf942f06dc0
Source dataset
uspto-grants-2007_01
Patent number
US07169921B2

Reaction notes

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