HCID 86676433, compound → HCID 67211343, compound

HRID 1401883Notes

Reaction equation

HRID 1401883 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C@:12]23[CH2:21][CH2:20][C@H:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][C@H:13]2OC(=S)O3)=[CH:8][CH:7]=1)[CH3:2]>C(OP(OCC)OCC)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH2:21][CH2:20][C@@H:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

3

Reactant 1

HCID 86676433HCID 86676433, compound

Product 1

HCID 67211343HCID 67211343, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent2×

Procedure

A solution of [4-((3aR,6S,7aR)-6-tert-Butyl-2-thioxo-tetrahydro-benzo[1,3]dioxol-3a-yl)-phenyl]-acetic acid ethyl ester (297 mg, 0.80 mmol) in triethylphosphite (3 mL) was slowly added to a solution of triethylphosphite (10 mL) heated to reflux—rate of addition was such that the reaction temperature exceeded 150. After refluxing overnight, the solvent was removed under vacuum and the crude reaction mixture was loaded on top of a silica column and eluted with an ethyl acetate/hexanes gradient to afford 145 mg of the title compound. 1H NMR (500 MHz, CDCl3): 7.32 (d, J=8 Hz, 2 H), 7.20 (d, J=8 Hz, 2 H), 6.10 (m, 1 H), 4.12 (q, J=7 Hz, 2 H), 3.57 (s, 2 H), 2.52-2.32 (m, 2 H), 2.26-2.18 (m, 1 H), 2-1.9 (m, 2 H), 1.38-1.2 (m, 5 H), 0.91 (s, 9 H).

Workup

  1. temperatureheated
  2. temperatureto reflux—rate of addition
  3. temperatureAfter refluxing overnight
  4. customthe solvent was removed under vacuum
  5. customthe crude reaction mixture
  6. washeluted with an ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-c0cf619ca4a14b22ac2481c36210fc34
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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