Reaction #1483031

Reaction equation

4-(tert-butyidiphenylsilyloxy)butanal

hydroxy ethylamine

→

12

2-(3-(tert-butyidiphenylsilyloxy)propyl)oxazolidine

Solvents

benzene

benzene

Conditions

Workup

1. 1
   workup.ADDITIONPowdered molecular sieves (4 Å, 600 mg) were added
2. 2
   Filtrationbefore being filtered through a 20 μm Millipore syringe
3. 3
   Filtrationfilter
4. 4
   Concentrationconcentrated

Procedure

A mixture of the 4-(tert-butyidiphenylsilyloxy)butanal (235 mg, 0.72 mmol) in benzene (3 ml) was added dropwise to a solution of hydroxy ethylamine (44 μL, 0.72 mmol) in benzene (3 mL). Powdered molecular sieves (4 Å, 600 mg) were added and the mixture was stirred for 1.5 h, before being filtered through a 20 μm Millipore syringe filter and concentrated. This gave 12 which was used directly and immediately in the synthesis of 13 (infra): 1H NMR (C6D6); δ1.18 (s, 9H), 1.65-1.82 (m, 2H), 2.62 (m, 2H), 3.33 (dd, 3H, J=6.1, 7.5 Hz), 3.69 (t, 3H, J=6.1 Hz), 4.26 (t, 1H), 7.23 (dd, 6H, J=1.9, 3.1 Hz), 7.79 (m, 4H).

Source