Sodium borohydride → tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

HRID 1747144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747144
[O:1]=[C:2]1[C@:6]2([CH:10]=[CH:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]2)[CH2:5][CH2:4][O:3]1.[BH4-].[Na+]>CO>[OH:3][CH2:4][CH2:5][C@@:6]1([CH2:2][OH:1])[CH2:7][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH:9]=[CH:10]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86708140tert-Butyl (5S,7S)-1-oxo-2-oxaspiro[4.4]non-8-en-7-ylcarbamate

Produkt 1

HCID 86708141tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the product of Step E (255.9 g, 1.01 mol) and MeOH (2 L) chilled to 2° C. was added NaBH4 (75 g) over ˜2.5 h. The reaction was quenched by addition of aqueous NH4Cl, concentrated under reduced pressure and the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with additional EtOAc. The combined organics were washed with brine, dried (MgSO4) and evaporated to give the product of Step F as a thick oil. 1H NMR (400 MHz, CHLOROFORM-d) d=5.74 (d, J=2.0 Hz, 2H), 4.81-4.92 (m, 1H), 4.67-4.79 (m, 1H), 3.71 (t, J=6.1 Hz, 2H), 3.50 (d, J=11.7 Hz, 2H), 2.14-2.28 (m, 2H), 1.70 (td, J=1.6, 6.2 Hz, 4H), 1.52-1.60 (m, 1H), 1.44 (s, 9H)

Aufarbeitung

  1. customThe reaction was quenched by addition of aqueous NH4Cl
  2. concentrationconcentrated under reduced pressure
  3. additionthe mixture was diluted with water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fae468aeb8654c4582e1ed5ef3cb6643
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150532B2

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