Isopropanol → HCID 86596901, compound

HRID 1455457Notes

Reaction equation

HRID 1455457 reaction equation
[CH:1]([S:4][CH2:5][C@@H:6]1[CH2:11][C:10](=[O:12])[CH2:9][CH2:8][C@@H:7]1[NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:3])[CH3:2].[C:24]12(CS(O)(=O)=O)C(C)(C)C(CC1)[CH2:27][C:25]2=[O:26].[CH3:39][CH:40](O)[CH3:41]>C(OC(C)C)(OC(C)C)OC(C)C>[CH:40]([O:12][C:10]1([O:26][CH:25]([CH3:27])[CH3:24])[CH2:9][CH2:8][C@H:7]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:6]([CH2:5][S:4][CH:1]([CH3:3])[CH3:2])[CH2:11]1)([CH3:41])[CH3:39]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 86596902HCID 86596902, compound

Product 1

HCID 86596901HCID 86596901, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-Solvent

Procedure

A sample of benzyl (1S,2R)-2-(isopropylthiomethyl)-4-oxocyclohexylcarbamate (8.66 g, 25.81 mMol) was dissolved in a mixture of iPrOH (50 mL) and triisopropyl orthoformate (50 mL) prior to the portionwise addition of camphorsulfonic acid (1.2 g, 5.16 mMol). After overnight stirring at rt, the reaction was quenched by addition of saturated sodium bicarbonate. Partitioned between EtOAc and water. The aq. layer was re-extracted with EtOAc. Combined organic layer was washed with brine and dried (MgSO4). Filtered, concentrated and flash chromatographed to yield benzyl (1S,2R)-4,4-diisopropoxy-2-(isopropylthiomethyl)cyclohexylcarbamate as a foamy solid (8.376 g, yield=74%)

Workup

  1. customthe reaction was quenched by addition of saturated sodium bicarbonate
  2. customPartitioned between EtOAc and water
  3. extractionThe aq. layer was re-extracted with EtOAc
  4. washCombined organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltered
  7. concentrationconcentrated
  8. customflash chromatographed

Sources & evidence

ORD record
ord-b7499ab569f94c4cabf122c43c57d9ae
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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