Boc-Hyp(Bzl)-OH → HCID 14821719, Verbindung

HRID 750021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750021
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21](O)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 11860409Boc-Hyp(Bzl)-OH

Produkt 1

HCID 14821719HCID 14821719, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(2S,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (960 mg, 3 mmol) in THF (5 mL) was cooled to 0° C. using ice-water bath. Then 1M solution of BH3 (6mL, 6 mmol) in THF was added under nitrogen over period of 30 min. Reaction was stirred at 0° C. for 2 h and at rt for another 1 h. Reaction mixture was poured over ice water and product was extracted with EtOAc. Organic layers were combined, washed with water, brine, saturated sodium bicarbonate, dried over anhydrous MgSO4 and concentrated to give the crude product. It was used in next step without purification (900 mg, 97%); MS; m/z 286.1 (M+H); 1H NMR (400 MHz, DMSO-4-d6); δ 1.90 (m, 1H), 2.01 (m, 1H), 3.09 (m, 1H), 3.34 (m, 1H), 4.12 (m, 2H); 4.27 (m, 1H), 4.46 (m, 1H), 5.46 (br s, 2H), 6.92 (d, J=6.8 Hz, 2H), 7.02 (s, 4H), 7.08 (t, J=5.6 Hz, 1H), 7.35 (m, 2H), 9.09 (br s, 1H), 9.62 (br s, 3H);

Aufarbeitung

  1. customReaction
  2. customReaction mixture
  3. extractionwas extracted with EtOAc
  4. washwashed with water, brine, saturated sodium bicarbonate
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b9787c980e948a8a4a403e15099523b
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402684B2

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