Carbon dioxide methanol → (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

HRID 877830Notes

Reaction equation

HRID 877830 reaction equation
[CH3:1][C:2]12[O:7][CH:6]1[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3]2.C(=O)=O.CO>CO>[CH3:1][C@:2]12[O:7][C@H:6]1[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3]2

Participants

4

Reactant 2

HCID 21973728Carbon dioxide methanolHCID 86707906Benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 86707907(1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A racemic mixture of benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (12 g) was resolved under the following conditions: Column: Chiralpak AD-H (5×25 cm, 5 μm), BPR pressure: 100 bars; temperature: 40° C.; flow rate: 290 mL/min; mobile Phase: CO2/MeOH (90/10); Detector Wavelength: 215 nm; injection: 0.83 mL with cycle time 2.6 min; sample preparation: 12.0 g/400 mL MeOH, 30.0 mg/mL. The desired (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate was obtained as the slower eluting peak (4.5 g).

Workup

  1. custom40° C.
  2. customwith cycle time 2.6 min
  3. customsample preparation

Sources & evidence

ORD record
ord-59f7904b248a4ab6b0d9c41a7a35a77b
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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