Sodium borohydride → (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate

HRID 2039915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039915
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:29])=[C:6]([C@H:8]([O:22][CH2:23][C:24](OCC)=[O:25])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:29])=[C:6]([C@H:8]([O:22][CH2:23][CH2:24][OH:25])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:10]2)[CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 58011572(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 58011515(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate (8 g, 18.8 mmol) in MeOH (300 mL) was added NaBH4 (5.6 g, 0.15 mol) in portions while the temperature was lower than 40° C. After addition, the mixture was stirred overnight. The solvent was removed in vacuo to the residue, which was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated to give crude (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate (7 g), which was used in the next step without purification.

Aufarbeitung

  1. customwas lower than 40° C
  2. additionAfter addition
  3. customThe solvent was removed in vacuo to the residue, which
  4. customwas partitioned between water and EtOAc
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3f7c888fb5e84418807bef4d8e4e40ea
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580823B2

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