Citric Acid → tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2167441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167441
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12](/[C:18](/[C:26]#[N:27])=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:26]#[N:27])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 66978138(Z)-tert-Butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Produkt 1

HCID 66978151tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 0.178 mmol of (Z)-tert-butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2 ml ethanol were added at 0° C. 0.178 mmol of sodium borohydride. The mixture was allowed to warm to room temperature and stirred for 3 d. The mixture was poured on ice water and citric acid (5%) was added until acidic. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and filtered. Evaporation of the solvent gave 61.2 mg (95%) of a crude slightly yellow oil, that was directly submitted to Boc deprotection.

Aufarbeitung

  1. additionwere added at 0° C
  2. additionwas added until acidic
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent
  8. customgave 61.2 mg (95%) of a crude slightly yellow oil, that

Quellen und Nachweise

ORD-Eintrag
ord-ececcb87103a49a7acc07a05b6127085
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045459B2

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