Imidazole → (3S)-3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)morpholine

HRID 1422293Notes

Reaction equation

HRID 1422293 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C@H:2]1[CH2:7][OH:8].[C:9]([Si:13]([CH3:16])([CH3:15])Cl)([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1>ClCCl>[Si:13]([O:8][CH2:7][C@@H:2]1[CH2:3][O:4][CH2:5][CH2:6][NH:1]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1514269(R)-3-Hydroxymethylmorpholine

Product 1

HCID 22309119(3S)-3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)morpholineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R)-Morpholine-3-methanol (84.8 mg, 0.72 mmol), t-butyldimethylchlorosilane (0.11 g, 0.72 mmol), and imidazole (59.1 mg, 0.87 mmol) were allowed to react in 1 mL of dichloromethane at room temperature for 2 hours. The reaction product was purified by silica gel chromatography (dichloromethane:methanol:acetone=15:1:0.5) to obtain (3S)-3-(t-butyldimethylsilyloxy)methylmorpholine (0.15 g, 92%) as a colorless oil.

Workup

  1. customThe reaction product was purified by silica gel chromatography (dichloromethane:methanol:acetone=15:1:0.5)

Sources & evidence

ORD record
ord-25447737ee9c4805933f431f70e30a96
Source dataset
uspto-grants-2000_06
Patent number
US06080859

Reaction notes

Loading…