Benzyl chloroformate → Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 251471Notes

Reaction equation

HRID 251471 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3](=[O:9])[CH2:2]2.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[O:9]=[C:3]1[CH2:2][CH:1]2[N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 4344538-Azabicyclo(3.2.1)octan-3-one

Product 1

HCID 14682535Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-azabicyclo[3.2.1]octan-3-one (5.10 g; 31.55 mmol) was dissolved in CH2Cl2 (50 mL) and treated with benzyl chloroformate (4.29 mL; 5.11 g; 29.98 mmol) DIPEA (16.48 mL; 12.23 g; 94.66 mmol) was added drop-wise (exothermic reaction). The resulting clear solution was allowed to stir at room temperature for 30 min and was subsequently diluted with 100 mL CH2Cl2. The organic phase was washed with 1 N HCl (2×100 mL), dried on Na2SO4 and concentrated to provide the crude product (7.2 g). 1H-NMR (400 MHz, CDCl3) δ 7.38 (m, 5H), 5.22 (s, 2H), 4.62 (s, 2H), 2.67 (m, 2H), 2.38 (d, J=15.9 Hz, 2H), 2.12 (m, 2H), 1.71 (dd, J=15.0, 7.2 Hz, 2H).

Workup

  1. additionwas added
  2. customdrop-wise (exothermic reaction)
  3. washThe organic phase was washed with 1 N HCl (2×100 mL)
  4. customdried on Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a5c7a9263cd8484eb2811f0becd8a203
Source dataset
uspto-grants-2011_01
Patent number
US07863449B2

Reaction notes

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