Sodium cyanoborohydride → (R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate

HRID 2071112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071112
O[CH2:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[O:6][CH:7]=1.[BH3-]C#N.[Na+]>CN(P(N(C)C)(N(C)C)=O)C.[I-].C[P+](OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>[CH3:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[O:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 5003444Sodium cyanoborohydrideHCID 86647435(R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate

Produkt 1

HCID 86647436(R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylateAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2735090Methyltriphenoxyphosphonium iodideKatalysatorHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate (1.1 g, 3.64 mmoles) in HMPA (18 mL), was added methyltriphenoxyphosphonium iodide (3.29 g, 7.28 mmoles) and stirred for 30 min. Then NaCNBH3 was added and the reaction was heated at 50° C. for 3 h and poured into 100 mL of ice-cold water and extracted with ether (2×100 mL). The organic layer was dried on Na2SO4, concentrated, and chromatographed on silica gel (50% ethyl acetate/50% hexanes) to yield 180 mg of (R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate.

Aufarbeitung

  1. extractionextracted with ether (2×100 mL)
  2. customThe organic layer was dried on Na2SO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (50% ethyl acetate/50% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d52c605f8578400da0032e7ef615ac0a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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