Tempo → HCID 118061571, compound

HRID 920783Notes

Reaction equation

HRID 920783 reaction equation
[OH:1][CH2:2][C:3]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5]([O:9][CH3:10])([O:7][CH3:8])[CH2:4]1.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O.CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH:2]([C:3]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5]([O:7][CH3:8])([O:9][CH3:10])[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 2724126TempoHCID 73357407Acetic acid;iodosylbenzeneHCID 118061684HCID 118061684, compound

Product 1

HCID 118061571HCID 118061571, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropyl 1-(hydroxymethyl)-3,3-dimethoxycyclobutanecarboxylate (2.3 g, 9.90 mmol) in DCM (45 mL) was added iodosobenzene diacetate (4.78 g, 14.85 mmol) and TEMPO (0.155 g, 0.990 mmol) and the mixture was stirred at RT for 8 h. The reaction mass was diluted with DCM (25 mL), washed with and a 10% aq. solution of NaHCO3, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 5% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 304A as a pale yellow liquid (1.3 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.62 (s, 1H), 4.96 (s, 1H), 3.04 (d, J=7.18 Hz, 6H), 2.59-2.66 (m, 2H), 2.47 (m, 2H), 1.20 (d, J=6.42 Hz, 6H).

Workup

  1. washwashed with and a 10% aq. solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 5% MeOH in CHCl3)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-ee7db9d2e11146c7a396ebe26d72037b
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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