Water → cis-3-(4-Chlorophenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600718Notes

Reaction equation

HRID 600718 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](Cl)=[N:21][OH:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>C(OCC)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:12][C@H:11]2[C@H:10]([C:20]([C:17]3[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=3)=[N:21][O:22]2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride2×HCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 68971118cis-3-(4-Chlorophenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To N-Boc pyrroline (480 mg; 2.83 mmol) and chloro oxime 2a (557 mg; 2.93 mmol) in ethyl acetate (15 mL), was added dropwise triethylamine (0.4 mL) in ethyl acetate (15 mL). The reaction mixture was stirred at room temperature for 24 hours. An additional portion of chloro oxime 2a (234 mg; 1.23 mmol) and triethylamine were added. After stirring overnight, the reaction mixture was poured into water (50 mL) and extracted. The organic layer was dried (MgSO4), filtered and evaporated. Chromatography with 30% ethyl acetate/hexanes yielded 3a as a white solid.

Workup

  1. stirringAfter stirring overnight
  2. extractionextracted
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-18cc9b1773e14bb2b11ab3ac06e85a07
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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