Water → HCID 58092771, compound

HRID 1807655Notes

Reaction equation

HRID 1807655 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) was 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) was added. The RM was then allowed to warm to −30° C. over 3 h and water was added. The aqueous layer was extracted with DCM, the combined organic layers evaporated and the residue was then purified by normal phase chromatography, eluting with DCM, to give the title compound as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-5c541b11b09f4ae0a57982ad84a169f6
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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