Dimethyl Sulfoxide → (2R,3S,5S)-5-Formyl-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 500008Notes

Reaction equation

HRID 500008 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][OH:14])[CH2:11][C@@H:10]([CH:15]([CH3:17])[CH3:16])[C@@H:9]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(N(C(C)C)CC)(C)C.CS(C)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[O:14])[CH2:11][C@@H:10]([CH:15]([CH3:17])[CH3:16])[C@@H:9]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 81531DiisopropylethylamineHCID 11998746(2R,3S,5S)-5-Hydroxymethyl-3-isopropyl-2-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11998864(2R,3S,5S)-5-Formyl-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl esterYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Alternatively, to a solution of 1.1 g of the alcohol 6 in 10 mL of dichloromethane is added 0.4 g of pyridine, 1.1 g of diisopropylethylamine and 2.0 g of dimethyl sulfoxide. The mixture is cooled to −5° C. and 0.6 g of sulfur trioxide-pyridine complex is added in four portions over a period of 2 h. The reaction is quenched by addition of 2.5 mL of water and acidified by addition of 1 mL of 37% hydrochloric acid. The phases are separated and the organic phase washed with 2.5 mL of water, dried over sodium sulfate and the solvent removed in-vacuum, to afford e.g. 0.88 g of the aldehyde 7 as an oil.

Workup

  1. addition0.6 g of sulfur trioxide-pyridine complex is added in four portions over a period of 2 h
  2. customThe reaction is quenched by addition of 2.5 mL of water
  3. additionacidified by addition of 1 mL of 37% hydrochloric acid
  4. customThe phases are separated
  5. washthe organic phase washed with 2.5 mL of water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in-vacuum

Sources & evidence

ORD record
ord-a29ad50027144d48aed1d630d16763b5
Source dataset
uspto-grants-2010_08
Patent number
US07767831B2

Reaction notes

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