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

HRID 1395849노트

반응식

HRID 1395849 반응식
[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

참가 물질

4

반응물 2

HCID 700EthanolamineHCID 108711124-(Tert-butyldiphenylsilyloxy)butanal

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c0e0afbe08564e1ab917b317ae7eb9ba
출처 데이터셋
uspto-grants-2014_12
특허 번호
USRE045272E1

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