Dimethyl Sulfide → HCID 69333353, compound

HRID 350467Notes

Reaction equation

HRID 350467 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH:9]1[C:22](O)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH:9]1[CH2:22][OH:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 23511756(2S,4S)-1-(Tert-butoxycarbonyl)-4-(2,4-difluoro-phenoxy)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69333353HCID 69333353, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(tert-butoxycarbonyl)4-(2,4-difluorophenoxy)pyrrolidine-2-carboxylic acid (2.55 g, 7.43 mmol) in THF (50 ml) was added BH3.DMS (452 ul, 7.43 mmol). The mixture was heated at reflux overnight. After cooling to room temperature, the mixture was concentrated in vacuo and quenced by the addition of H2O (100 ml). The mixture was extracted with CHCl3 (2×200 ml), dried over MgSO4, and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)-2-pyrrolidinylmethanol (1.76 g, 72%) as a colorless oil. 1H-NMR (CDCl3) δ 1.45 (s, 9 H), 2.28–2.36 (m, 2 H), 3.58–4.99 (series of m, 8 H), 6.74–6.90 (m, 3 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. additionquenced by the addition of H2O (100 ml)
  5. extractionThe mixture was extracted with CHCl3 (2×200 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-cd2f902c4d7e4c6c8485b2ff999a2f4b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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