Water → HCID 69333353, compound

HRID 354404Notes

Reaction equation

HRID 354404 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.O>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

5

Reactant 3

HCID 962WaterHCID 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 concntrated 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) δ1.45 (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. extractionThe mixture was extracted with CHCl3 (2×200 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-e2eab9d565204faf95e61d9746085aa1
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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