Diisopropylethylamine → HCID 58109191, compound

HRID 2037395Notes

Reaction equation

HRID 2037395 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)([OH:6])[CH3:5].CCN(C(C)C)C(C)C.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOCC>[Cl:13][C:9]1[CH:8]=[C:7]([C:4]2([CH3:5])[O:6][C:24](=[O:26])[NH:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58109252HCID 58109252, compound

Product 1

HCID 58109191HCID 58109191, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of crude 4-amino-2-(3-chlorophenyl)butan-2-ol (550 mg) and i-Pr2NEt (1 mL, 5.5 mmol) in CH2Cl2 was cooled in an ice bath and solid triphosgene (286 mg, 0.96 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (150 mL), washed with 5% aq HCl (50 mL) and satd aq NaHCO3 (50 mL) and dried over MgSO4. Removal of the solvent left a brown oil (590 mg) which was purified by chromatography on a 12-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford 6-(3-chlorophenyl)-6-methyl-1,3-oxazinan-2-one (57 mg).

Workup

  1. washwashed with 5% aq HCl (50 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. waitleft a brown oil (590 mg) which
  5. customwas purified by chromatography on a 12-g silica cartridge
  6. washeluted with a 0-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-d1be24ddf48140608b8e616a4bbf5aef
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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