Tetrahydrofuran → tert-butyl(2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 255353Notes

Reaction equation

HRID 255353 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH:22]=[CH2:23])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C1C[O:36]CC1>O.[OH-].[Na+].OO.C(OCC)(=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH2:22][CH2:23][OH:36])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 66774108tert-butyl(2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-vinylpiperidine-1-carboxylate2×

Product 1

HCID 66774126tert-butyl(2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 784Hydrogen PeroxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-vinylpiperidine-1-carboxylate (Intermediate 188, 1.39 g) in THF (20 mL) at 0° C. was added 9-BBN (0.5 M, 15 mL). After 45 minutes, the reaction was diluted with water (3 mL), 3 N NaOH (12 mL) and 30% H2O2 (12 mL). After 15 minutes, the reaction was allowed to warm to room temperature. After 30 minutes, the reaction was diluted with ethyl acetate, washed with 1 N HCl, NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. Chromatography on silica gel with a gradient of 0-5% methanol in methylene chloride gave 1.27 g of product.

Workup

  1. waitAfter 15 minutes
  2. waitAfter 30 minutes
  3. washwashed with 1 N HCl, NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-90aec727cfb744a7a0f012b7f87662c5
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

Loading…