Hexachloroacetone → HCID 69296253, compound

HRID 899778Notes

Reaction equation

HRID 899778 reaction equation
O[C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:4]=[CH:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:35]C(Cl)(Cl)C(C(Cl)(Cl)Cl)=O>>[C:12]([O:11][C:9]([NH:8][C@H:5]1[CH2:6][CH2:7][C@@H:2]([Cl:35])[CH:3]=[CH:4]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 8303HexachloroacetoneHCID 11776TriphenylphosphineHCID 69157188Carbamic acid, [(1R,4R)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester, rel-

Product 1

HCID 69296253HCID 69296253, compoundYield 62%

Procedure

To a mixture of trans-1-hydroxy-4-(tert-butoxycarbonylamino)-2-cyclohexene (2.93 g, 13.8 mmol) in hexachloroacetone (70 mL) was added triphenylphosphine (7.51 g, 28.6 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated and the thus obtained oil was purified by column chromatography on silica gel (10:1 hexanes-ethyl acetate) and provided 1.98 g (62%) of cis-1-(tert-butoxycarbonylamino)-4-chloro-2-cyclohexene as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe thus obtained oil was purified by column chromatography on silica gel (10:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-33d1722462ae402499626ef779371711
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

Loading…