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(S)-4-((tert-Butyldimethylsilyl)oxy)butan-2-ol → (S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

HRID 245717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 245717
[Si:1]([O:8][CH2:9][CH2:10][C@@H:11]([OH:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:14]([C:17]1[CH:22]=[CH:21][C:20]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:19][C:18]=1[O:32][CH3:33])=[C:15]=[O:16]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:33][O:32][C:18]1[CH:19]=[C:20]([B:23]2[O:27][C:26]([CH3:28])([CH3:29])[C:25]([CH3:30])([CH3:31])[O:24]2)[CH:21]=[CH:22][C:17]=1[NH:14][C:15](=[O:16])[O:13][C@H:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:12]
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Komponenten

5

Edukt 2

HCID 10998136(S)-4-((tert-Butyldimethylsilyl)oxy)butan-2-olHCID 866746582-(4-Isocyanato-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 67365296(S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To (S)-4-(tert-butyldimethylsilyloxy)butan-2-ol (1.649 mmol, 337 mg) in dichloromethane (4 ml) were added mol sieves (4A), 2-(4-isocyanato-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.374 mmol, 378 mg) and 4-dimethylaminopyridine (0.275 mmol, 33.6 mg) were added and the mixture was stirred at 40° C. (oil bath temperature) for 18 hours. The mol sieves were removed by filtration and the filtrate washed with water, dried (sodium sulfate) and concentrated in vacuo to give a crude product which was purified by column chromatography (silica gel, heptanes with gradient 10% to 50% of ethyl acetate) to afford (S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (443 mg). Tetrabutylammonium fluoride (1M in tetrahydrofuran, 1.22 mmol, 1.22 ml) was added to (S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (240 mg) in tetrahydrofuran (1 ml) at room temperature. After 20 hours water was added to the reaction mixture, extracted with dichloromethane, the organic extract dried (sodium sulfate) and concentration in vacuo to yield (S)-4-hydroxybutan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (268 mg) which was used in the next step without further purification.

Aufarbeitung

  1. additionwere added
  2. customThe mol sieves were removed by filtration
  3. washthe filtrate washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas purified by column chromatography (silica gel, heptanes with gradient 10% to 50% of ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-740425fee6084b7791f0fbed821e3491
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658794B2

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