(Phenylmethoxy)acetaldehyde → phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylate

HRID 1366640

Reaktionsgleichung

Reaktionsgleichung von HRID 1366640
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH2:18]([O:25][CH2:26][CH:27]=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:27][CH2:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 40425199Benzyl (2S)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 66935999phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate (commercially available) (1 g, 4.3 mmol) and benzyloxyacetaldehyde (0.9 mL, 6.4 mmol) in DCM (50 mL) was stirred for 30 minutes, and then NaBH(OAc)3 (1.36 g, 6.4 mmol) was added. The reaction was stirred overnight before being quenched with 1 M NaOH. The phases were separated and the aqueous layer was extracted with DCM. The combined organics were washed with brine, dried over sodium sulfate and concentrated to a crude residue, which was purified by silica gel chromatography (5-95% EtOAc in hexane) yielding phenylmethyl (2S)-2-methyl-4-{2-[(phenylmethyl)oxy]ethyl}-1-piperazinecarboxylate (0.93 g, 58%). LCMS: (M+H)+: 369.1

Aufarbeitung

  1. custombefore being quenched with 1 M NaOH
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a crude residue, which
  7. customwas purified by silica gel chromatography (5-95% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ba015d2a15f246e69cfccaecc06d6998
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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