Water → 79091-88-6

HRID 920754Notes

Reaction equation

HRID 920754 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:6][CH2:5][C@@H:4]1[C:7]([O:9][CH3:10])=[O:8].C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.CC1(C)N([O])C(C)(C)CCC1.O>C(Cl)Cl>[CH:2]([C@@H:3]1[CH2:6][CH2:5][C@H:4]1[C:7]([O:9][CH3:10])=[O:8])=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 2724126TempoHCID 21865429Bis(acetoxy)iodobenzeneHCID 93501228HCID 93501228, compound

Product 1

HCID 1272133479091-88-6Yield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1S,2R)-methyl 2-(hydroxymethyl)cyclobutanecarboxylate (100 mg, 0.694 mmol) in DCM (5 mL) was added bis(acetoxy)iodobenzene (335 mg, 1.040 mmol) and TEMPO (10.84 mg, 0.069 mmol) at 0° C. The temperature of the reaction was allowed to slowly warm to RT and stirred for 6 h. Water was added to reaction mass and the compound was extracted with DCM (3×10 mL). The combined organic layer was dried over Na2SO4, filtered and the filtrate evaporated. The crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 40% EtOAc in petroleum ether). Fractions containing the product were combined and evaporated to afford Intermediate 238A as yellow oil (50 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.62 (s, 1H) 3.71 (s, 3H), 3.69-3.36 (m, 2H), 2.31-2.16 (m, 4H).

Workup

  1. extractionthe compound was extracted with DCM (3×10 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customThe crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 40% EtOAc in petroleum ether)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-12dfd865d485494da03052822a7b0ad6
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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