Dimethyl Sulfoxide → HCID 86587786, compound

HRID 350465Notes

Reaction equation

HRID 350465 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C@H:9]1[CH2:20][OH:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][C@H:9]1[CH:20]=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 59838273HCID 59838273, compound

Product 1

HCID 86587786HCID 86587786, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylmethanol (2.75 g, 9.37 mmol), Et3 N (7.84 ml, 56.2 mmol), DMSO (6.66 ml, 9.37 mmol) in CH2Cl2 (30 ml) at 0° C. was added SO3-pyridine (4.47 g, 28.1 mmol), then the resulting mixture was allowed to raise to room temperature. After 2.5 h stirring, the mixture was concentrated in vacuo. To the resulting mixture was added water and extracted with Et2O. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [100 g, CHCl3/acetone (5/1)] to give (2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidine carbaldehyde (2.54 g, 93%) as a yellow oil. 1H-NMR (CDCl3) δ 1.45 (s, 9H, one of isomers), 1.49 (s, 9H, one of isomers), 2.17 (br, 2H), 3.65–4.31 (m, 3H), 4.91 (br, 1H), 6.79 (d, J=7.8 Hz, 1H), 6.77 (m, 1H), 7.28 (m, 2H), 9.66 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionTo the resulting mixture was added water
  3. extractionextracted with Et2O
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel [100 g, CHCl3/acetone (5/1)]

Sources & evidence

ORD record
ord-146c7b4f73ae4671874b40b23ebc368a
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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