Tetrahydrofuran → HCID 131733444, compound

HRID 2277063Notes

Reaction equation

HRID 2277063 reaction equation
C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][C@H:22]([C:24]1[CH:25]=[C:26]([CH:41]=[CH:42][CH:43]=1)[O:27][CH2:28][C@@H:29]1[CH2:33][CH2:32][CH2:31][N:30]1[C:34](OC(C)(C)C)=O)[OH:23])=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO.C(Cl)Cl>[OH:23][C@@H:22]([C:24]1[CH:43]=[CH:42][CH:41]=[C:26]([O:27][CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][N:30]2[CH3:34])[CH:25]=1)[CH2:21][CH2:20][NH:19][C:17](=[O:18])[O:16][C:12]([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 90405868HCID 90405868, compound

Product 1

HCID 131733444HCID 131733444, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Anhydrous THF (5 mL) was cooled to 0° C. and LiAlH4 (0.016 g, 0.44 mmol) was added. (S)-tert-butyl 2-((3-((R)-3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)pyrrolidine-1-carboxylate (0.1 g, 0.22 mmol) was slowly added to reaction mixture and then kept at room temperature for 4 hrs. After completion of reaction as judged by TLC (10% MeOH/CH2Cl2) the reaction mixture was quenched with EtOAc followed by saturated Na2SO4, extracted with EtOAc and organic layer was concentrated under reduced pressure to give tert-butyl ((R)-3-hydroxy-3-(3-(((S)-1-methylpyrrolidin-2-yl)methoxy)phenyl)propyl)carbamate as a light yellow oil which was used in the next step without additional purification. Yield (0.060 g, 75%).

Workup

  1. customAfter completion of reaction
  2. customwas quenched with EtOAc
  3. extractionextracted with EtOAc and organic layer
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a496b74f34a4737ba5960b79aeabf38
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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