Phosphate → HCID 86592532, compound

HRID 1374435Notes

Reaction equation

HRID 1374435 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C:14]([C:15]([O:17]C)=O)=[CH:13][CH2:12][N:11]1[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:26][Cl:27].C([Li])CCC.CCCCCC.P([O-])([O-])([O-])=O>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@@H:10]1[C:14]([C:15](=[O:17])[CH2:26][Cl:27])=[CH:13][CH2:12][N:11]1[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 1061PhosphateHCID 6333BromochloromethaneHCID 8058HexaneHCID 11439682HCID 11439682, compoundHCID 178418339Butyllithium

Product 1

HCID 86592532HCID 86592532, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-allyl 3-methyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (0.20 g, 0.55 mmol) and bromochloromethane (54 ml, 0.83 mmol) in THF (6 ml) was added at −90 to −80° C. a solution of n-butyllithium in hexane (1.59M, 0.52 ml, 0.83 mmol) over a 10 minutes period. After stirring for additional 30 minutes, the reaction mixture was poured into a mixture of ice (10 g) and phosphate buffer (pH 7.0, 10 ml). After ethyl acetate was added and the mixture was separated with a separating funnel, the aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel (27 g) chromatography to give allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(chloroacetyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (163 mg, 79%).

Workup

  1. customthe mixture was separated with a separating funnel
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customthe organic solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel (27 g) chromatography

Sources & evidence

ORD record
ord-ef8bd0c089d145e08eb0091183d639ea
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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