Water → HCID 58092771, compound

HRID 1430134Notes

Reaction equation

HRID 1430134 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]([Cl:21])([Cl:20])[C@@H:11]1[N:15]2[CH2:16][CH2:17][CH2:18][C@H:14]2[C:13](=[O:19])[O:12]1.[CH3:22][O:23][CH2:24]Cl.O>C1COCC1>[CH3:22][O:23][CH2:24][C@@:14]12[CH2:18][CH2:17][CH2:16][N:15]1[C@@H:11]([C:10]([Cl:9])([Cl:20])[Cl:21])[O:12][C:13]2=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 2724682Lithium diisopropylamideHCID 10944680HCID 10944680, compound

Product 1

HCID 58092771HCID 58092771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A 1M of solution of lithium diisopropylamide in a 3:5 mixture of hexanes/THF (8.25 ml) is added dropwise to (3R,7aS)-3-trichloromethyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (1.51 g, prepared as described by Wang and Germanas Synlett 1999, 33-36.) in THF (5 ml) at −78° C. After stirring 30 minutes at −78° C. methoxymethylchloride (1.14 ml) is added. The reaction mixture is then allowed to warm to −30° C. over 3 hours and water is added. The aqueous layer is extracted with dichloromethane, the combined organic layers evaporated and the residue is then purified by normal phase chromatography, eluting with dichloromethane, to give the title compound as a pale yellow oil.

Workup

  1. additionis added
  2. extractionThe aqueous layer is extracted with dichloromethane
  3. customthe combined organic layers evaporated
  4. customthe residue is then purified by normal phase chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-72ad3620854c488db3e85dfd48735367
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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