Sodium cyanoborohydride → Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

HRID 1867329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867329
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([OH:19])([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].[CH3:20][C:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH2:22][CH:23]=O>CO.CC(O)=O.CCOC(C)=O>[OH:19][C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][CH2:23][CH2:22][C:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH3:20])([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]

Komponenten

7

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateHCID 210728384-(2-Aminophenyl)heptan-4-ol

Produkt 1

HCID 86600980Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.40 g (22.27 mmol) of sodium cyanoborohydride is added to a solution of 3.10 g (14.05 mmol) of 4-(2-aminophenyl)heptan-4-ol and 3.60 g (17.88 mmol) of tert-butyl (1,1-dimethyl-3-oxopropyl)carbamate in MeOH (40 mL) and AcOH (6 mL). The mixture is stirred for 16 hours at RT, diluted with EtOAc, and washed with 0.5 M aqueous KHSO4 and saturated aqueous NaCl, dried with sodium sulfate, and evaporated down in vacuo. The crude product is used in the next reaction step without any further purification. Yield: 6.00 g (quantitative yield).

Aufarbeitung

  1. washwashed with 0.5 M aqueous KHSO4 and saturated aqueous NaCl
  2. dry with materialdried with sodium sulfate
  3. customevaporated down in vacuo
  4. customThe crude product is used in the next reaction step without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-b7583657aefb4139b6ff362811635af5
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632834B2

Notizen zur Reaktion

Wird geladen…