Water → (S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetate

HRID 525325

Reaktionsgleichung

Reaktionsgleichung von HRID 525325
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:5].[OH:13][CH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[OH:13][CH:14]1[CH2:19][CH2:18][CH:17]([NH:5][C@@H:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([O:2][CH3:1])=[O:12])[CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5437064-HydroxycyclohexanoneHCID 1201451Methyl phenylglycinate, L-HCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 89814327(S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

(S)-(+)-2-Phenylglycine methyl ester (commercially available from Sigma-Aldrich, Milwaukee, Wis., 433 g, 2.146 mol) was added to a solution of 4-hydroxycyclohexanone (245 g, 2.146 mol) in DCE (8.5 L). Sodium triacetoxyborohydride was added (910 g, 4.292 mol), and the mixture was stirred at room temperature under nitrogen for 23 hours. Water (3 L) was added to quench the reaction, and the organic layer was separated. The aqueous phase was extracted with DCM (4 L×2) and the organic layers were combined, dried, filtered and concentrated. The residue was purified by column chromatography (gradient elution with 100% DCM to DCM/MeOH=25:1) to afford (S)-methyl 2-((4-hydroxycyclohexyl)amino)-2-phenylacetate (197 g, 35%) (mixture of cis and trans). m/z (ESI) 264 (M+H)+.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was separated
  4. extractionThe aqueous phase was extracted with DCM (4 L×2)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (gradient elution with 100% DCM to DCM/MeOH=25:1)

Quellen und Nachweise

ORD-Eintrag
ord-86b7ddc4ecfb4365b550de1dc67b1548
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340549B2

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