Water → [2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester

HRID 1376016Notes

Reaction equation

HRID 1376016 reaction equation
Br[N:2]1[C:6](=[O:7])CCC1=O.[CH2:9]([N:16]1[CH2:23][CH:22]2[O:24][CH:18]([CH2:19][N:20]([CH2:25][CH2:26]C(N)=O)[CH2:21]2)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH2:30]>CC(C)([O-])C.[K+].C(O)(C)(C)C>[C:10]([O:30][C:6](=[O:7])[NH:2][CH2:26][CH2:25][N:20]1[CH2:19][CH:18]2[O:24][CH:22]([CH2:23][N:16]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:17]2)[CH2:21]1)([CH3:15])([CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 69508490HCID 69508490, compound

Product 1

HCID 10144351[2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolvent2×HCID 23665647Potassium tert-butoxideSolvent

Procedure

N-Bromosuccinimide (6.0 g, 33 mmol) was added in portions over 1 minute to a solution of 3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propionamide (see step (i) above; 5 g, 12 mmol) in potassium tert-butoxide in tert-butanol (1 M, 81 mL) and tert-butanol (20 mL). The mixture was then heated at 60–65° C. for 30 minutes. The reaction was allowed to come to room temperature and then water (100 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered (washing the filter cake with ethyl acetate (50 mL)) and then the filtrate concentrated under reduced pressure to give the title compound as a brown oil (6.5 g, >100%).

Workup

  1. temperatureThe mixture was then heated at 60–65° C. for 30 minutes
  2. customto come to room temperature
  3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered (
  7. washwashing the filter cake with ethyl acetate (50 mL)) and then the filtrate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e505efec21c4a66b414d54148d24c08
Source dataset
uspto-grants-2007_01
Patent number
US07169921B2

Reaction notes

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