Ethyl diazoacetate → 3-Tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

HRID 455284Notes

Reaction equation

HRID 455284 reaction equation
[N:1]1([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>C(Cl)Cl>[CH:3]12[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:4]1[CH2:5][N:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2]2

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 235533633-Tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylateYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10.0 g, 59.1 mmol) and Rh(OAc)2 (500 mg) in CH2Cl2 (200 mL) was added a solution of ethyl diazoacetate (8.14 g, 71.5 mmol) in CH2Cl2 (80 mL) over 12 h with a syringe pump. The reaction was filtered through celite, concentrated under vacuum and purified by column chromatography (silica gel) using 0 to 45% EtOAc in hexanes to afford ester 1 (6.70 g, 44%) as a clear straw colored oil; 1H-nmr (400 MHz, CDCl3) δ 4.18-4.03 (m, 2H), 3.71-3.53 (m, 2H), 3.39 (s, 2H), 2.04 (s, 2H), 1.42 (s, 9H), 1.28-1.19 (m, 3H).

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated under vacuum
  3. custompurified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-2eff2c80540a447792e75173f1a317f0
Source dataset
uspto-grants-2013_07
Patent number
US08497289B2

Reaction notes

Loading…