Chloral → (3S,7aR)-Tetrahydro-3-(trichloromethyl)-1H,3H-pyrrolo[1,2-c]oxazol-1-one

HRID 2285428Notes

Reaction equation

HRID 2285428 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[Cl:9][C:10]([Cl:14])([Cl:13])[CH:11]=O>C(#N)C>[Cl:9][C:10]([Cl:14])([Cl:13])[C@H:11]1[N:1]2[CH2:8][CH2:7][CH2:6][C@@H:2]2[C:3](=[O:5])[O:4]1

Participants

4

Reactant 2

HCID 6407ChloralHCID 8988D-Proline

Product 1

HCID 45158923(3S,7aR)-Tetrahydro-3-(trichloromethyl)-1H,3H-pyrrolo[1,2-c]oxazol-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To reactant (D)-Proline (4.6 g, 40 mmol) suspended in anhydrous acetonitrile (100 mL), was added 2,2,2-trichloroacetaldehyde (11.78 g, 80 mmol) slowly. The mixture was stirred at RT for 20 hour and was clear solution. After concentrated in vacuum, the residue was purified by CombiFlash on a 80 g silica gel column using EtOAC/Hexane as eluents to give (3S,7aR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one 155a: 3.63 g, 37%. 1H NMR (400 MHz, Chloroform-d) δ 5.14 (s, 1H), 4.10 (dd, J=8.9, 4.7 Hz, 1H), 3.40 (ddd, J=10.9, 7.8, 6.0 Hz, 1H), 3.11 (dt, J=11.4, 6.0 Hz, 1H), 2.21 (dtd, J=13.0, 8.5, 6.8 Hz, 1H), 2.09 (ddt, J=12.7, 7.0, 5.2 Hz, 1H), 1.91 (ddq, J=12.4, 6.7, 5.7 Hz, 1H), 1.81-1.64 (m, 1H).

Workup

  1. concentrationAfter concentrated in vacuum
  2. customthe residue was purified by CombiFlash on a 80 g silica gel column

Sources & evidence

ORD record
ord-48e28b8c421d4ff095c3cd072abcca17
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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