Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylate → tert-Butyl 7-[4-(4-cyanophenoxy)-2-butenyl]-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate

HRID 1596474Notes

Reaction equation

HRID 1596474 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]2.[C:17]([C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][CH:25]=[CH:26][CH2:27]Cl)=[CH:21][CH:20]=1)#[N:18]>CC#N>[C:17]([C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][CH:25]=[CH:26][CH2:27][N:7]2[CH2:8][CH:1]3[CH2:9][CH:5]([CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]3)[CH2:6]2)=[CH:21][CH:20]=1)#[N:18]

Participants

4

Reactant 2

HCID 22490264Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylateHCID 541838494-(4-Cyanophenoxy)-1-chloro-2-butene

Product 1

HCID 53669367tert-Butyl 7-[4-(4-cyanophenoxy)-2-butenyl]-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.13 g; 5 mmol; see Example F above) was added to a stirred solution of 4-(4-cyanophenoxy)-1-chloro-2-butene (1.04 g; 5 mmol; from step (a) above) in MeCN (25 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and partitioned between diethyl ether and KHS04 (0.3 M). The aqueous layer was treated with NaOH (2M) and subsequently extracted with CH2Cl2. The organic layer was washed with water, dried, concentrated and purified using column chromatography (CH2Cl2:MeOH; 95:5) to give the title compound (0.84 g; 2.1 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between diethyl ether and KHS04 (0.3 M)
  3. additionThe aqueous layer was treated with NaOH (2M)
  4. extractionsubsequently extracted with CH2Cl2
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-1debe97dd80649e788061843ba358e6a
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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