Methanol → HCID 68750810, compound

HRID 2065772Notes

Reaction equation

HRID 2065772 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.CO.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C@@H:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:53])[C@@H:43]([C:54]([OH:56])=[O:55])[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[CH3:1][O:55][C:54]([C@@H:43]1[C@H:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:53])[CH2:45][CH2:46][N:41]([C:39]([O:38][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:40])[CH2:42]1)=[O:56]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58248370HCID 58248370, compound

Product 1

HCID 68750810HCID 68750810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (2.66 g) in THF (30 ml) was added diethyl azodicarboxylate (1.58 mL) at 0° C. After 30 minutes, methanol (1.58 mL) and a solution of (3R,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester in THF (30 mL) were added subsequently at 0-5° C. The reaction mixture was stirred for 3 h at room temperature. The reaction was quenched with a saturated aqueous solution of NH4Cl, tert-butyl methyl ether was added, and the phases were separated. The inorganic one was extracted with tert-butyl methyl ether (3×100 ml). The combined organic layers were dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, CH2Cl2 to CH2Cl2/MeOH 95:5) yielded (3R,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a colorless gum, MS: 334.1 ([M+H])+.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of NH4Cl, tert-butyl methyl ether
  2. additionwas added
  3. customthe phases were separated
  4. extractionThe inorganic one was extracted with tert-butyl methyl ether (3×100 ml)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (SiO2, CH2Cl2 to CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-0d3567956a2246febe4c9b0b5639321f
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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