Water → Methyl 5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]ethyl]thiophene-2-carboxylate

HRID 1447423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1447423
[BH4-].[Na+].Br[CH2:4][C:5]([C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=1)=[O:6].O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:27])=[CH:21][CH:20]=1>CO>[OH:6][CH:5]([C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=1)[CH2:4][N:28]([CH:26]([CH3:27])[CH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 30164224-Methoxy-alpha-methyl-N-(phenylmethyl)benzeneethanamineHCID 4311764Sodium borohydrideHCID 13727591Methyl 5-(2-bromoacetyl)thiophene-2-carboxylate

Produkt 1

HCID 20550958Methyl 5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]ethyl]thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (3.14 g) was added to an ice-cold suspension of methyl 5-(bromoacetyl)thiophene-2-carboxylate (4.14 g) in methanol (250 ml). After 15 min the reaction mixture was poured into iced water (1000 ml) and extracted with ethyl acetate (5×200 ml). The dried (MgSO4) organic phase was evaporated to give a yellow oil, which was heted with [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine (5.18 g) at 100° for 16 h. The cooled reaction mixture was partitioned between water (400 ml) and ethyl acetate (3×400 ml), and the dried (MgSO4) organic phase was evaporated, giving the crude product as an oily brown solid (9.75 g). This was applied on silica to a short-path silica column (1000 g) eluted with cyclohexane 15% diethyl ether. The appropriate fractions (Rf 0.15) were combined and evaporated to give the ethanolamine (slightly impure) as an oily beige solid (2.4 g). TLC SiO2 (Et2O/cyclohexane, 1:1 ) Rf 0.39.

Aufarbeitung

  1. extractionextracted with ethyl acetate (5×200 ml)
  2. dry with materialThe dried (MgSO4) organic phase
  3. customwas evaporated
  4. customto give a yellow oil, which
  5. customThe cooled reaction mixture
  6. customwas partitioned between water (400 ml) and ethyl acetate (3×400 ml)
  7. dry with materialthe dried (MgSO4) organic phase
  8. customwas evaporated
  9. customgiving the crude product as an oily brown solid (9.75 g)
  10. washeluted with cyclohexane 15% diethyl ether
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-63549c912248403da238747cc6f9f115
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04316907

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