Diisopropylethylamine → HCID 178453955, compound

HRID 2391005Notes

Reaction equation

HRID 2391005 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.S(=O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridineHCID 178453956HCID 178453956, compound

Product 1

HCID 178453955HCID 178453955, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To trans-tert-butyl-4-(hydroxymethyl)cyclohexylcarbamate (8.0 g, 34.9 mmol) in DCM (180 mL) and DMSO (60 mL) at 0° C. is added DIPEA (24.37 mL, 140 mmol) and pyridine sulfur trioxide (22.21 g, 140 mmol) dissolved in DMSO (60 mL). The mixture is stirred at room temperature for 15 minutes and then is partitioned between 1M HCl and diethylether. The organic phase is separated and washed with 1M HCl, water then saturated brine. The mixture is dried (MgSO4) and solvent evaporated to give the expected product; [MH+MeCN]+ 269.

Workup

  1. customis partitioned between 1M HCl and diethylether
  2. customThe organic phase is separated
  3. washwashed with 1M HCl, water
  4. dry with materialThe mixture is dried (MgSO4) and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-51938ca73e144f409edc5e371f27fb53
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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