Ethanolamine → 2-(3-{[tert-Butyl(diphenyl)silyl]oxy}propyl)-1,3-oxazolidine

HRID 1395849Notes

Reaction equation

HRID 1395849 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH:22]=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:25][CH2:26][NH2:27]>C1C=CC=CC=1>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH:22]1[NH:27][CH2:26][CH2:25][O:23]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 108711124-(Tert-butyldiphenylsilyloxy)butanal

Product 1

HCID 598165432-(3-{[tert-Butyl(diphenyl)silyl]oxy}propyl)-1,3-oxazolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

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).

Workup

  1. additionPowdered molecular sieves (4 Å, 600 mg) were added
  2. filtrationbefore being filtered through a 20 μm Millipore syringe
  3. filtrationfilter
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c0e0afbe08564e1ab917b317ae7eb9ba
Source dataset
uspto-grants-2014_12
Patent number
USRE045272E1

Reaction notes

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