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

HRID 1664236Notes

Reaction equation

HRID 1664236 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-8d5efd8efdcb4aa989da35620ab31d3a
Source dataset
uspto-grants-2011_10
Patent number
US08039273B2

Reaction notes

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