Reaction #53397

Reaction equation

4-methylmorpholine N-oxide monohydrate

tert-butanol

30

N-Cbz-4-(4-Allyloxyphenyl)butylamine

NaHSO3

→

Compound 31

Yield 62.0%

N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine

Yield 62.0%

Solvents

acetone water

acetone water

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature overnight
2. 2
   workup.WAITthe stirring was continued for 15 min
3. 3
   OtherThe acetone was evaporated
4. 4
   workup.ADDITIONthe pH was adjusted to 5.5 by the addition of 2N HCl
5. 5
   Extractionthe mixture was extracted with ethyl acetate
6. 6
   OtherThe organic fraction was isolated
7. 7
   Dryingdried with sodium sulfate
8. 8
   Filtrationfiltered through silica gel

Procedure

A solution of osmium tetroxide (50 mg, 0.2 mmol) in tert-butanol (8 mL) was added to a solution of 4-methylmorpholine N-oxide monohydrate (1.2 g, 9.1 mmol) in 100 mL (1:1) acetone/water solution and the mixture was stirred for 10 min at room temperature. After this time, 30 (3.1 g, 9.0 mmol) was added in 50 mL (1:1) acetone/water solution. The reaction mixture was stirred at room temperature overnight, then NaHSO3 (0.5 g) was added and the stirring was continued for 15 min. The acetone was evaporated and the pH was adjusted to 5.5 by the addition of 2N HCl then the mixture was extracted with ethyl acetate. The organic fraction was isolated, dried with sodium sulfate, and filtered through silica gel. Compound 31 (2.1 g, 62%) was isolated as a white solid after removing the solvent and drying under vacuum. 1H NMR (300 MHz, DMSO-d6) δ 1.48 (m, 2H), 1.50 (m, 2H), 2.46 (m, 2H), 3.00 (m, 2H), 3.43 (m, 2H), 3.80 (m, 2H), 3.93 (t, 1H), 4.66 (d, 1H), 4.99 (s, 2H), 6.82 (d, 2H), 7.07 (d, 2H), 7.26 (s, 1H), 7.33 (s, 5H).

Source