Phenol → HCID 90405868, compound

HRID 2277062Notes

Reaction equation

HRID 2277062 reaction equation
S([O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(C1C=CC(C)=CC=1)(=O)=O.C1(O)C=CC=CC=1.[OH:32][C@@H:33]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46](O)[CH:45]=1)[CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].C([O-])(C)(C)C.[K+]>CN(C=O)C>[C:39]([O:38][C:37]([NH:36][CH2:35][CH2:34][C@H:33]([C:44]1[CH:49]=[C:48]([CH:47]=[CH:46][CH:45]=1)[O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[OH:32])=[O:43])([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 996PhenolHCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 90405868HCID 90405868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate (1.6 g, 5.4 mmol), phenol (7, Intermediate I) (0.8 g, 2.9 mmol), t-BuO−K+ (0.5 g, 4.5 mmol) in anhydrous DMF (5 mL) was heated at +45° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, partitioned between EtOAc and 5% NaOH, organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure. Purification by column chromatography gave (S)-tert-butyl 2-((3-((R)-3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)pyrrolidine-1-carboxylate as a light yellow oil. Yield (0.8 g, 59%).

Workup

  1. temperaturewas heated at +45° C. for 16 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between EtOAc and 5% NaOH, organic layer
  4. dry with materialwas dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-c8cbe2f514794d03ba127febf730f06f
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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