1,2-Dichloroethane → 1-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-piperidine-2-carboxylic acid

HRID 525467

Reaktionsgleichung

Reaktionsgleichung von HRID 525467
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].Cl.[C:11]([CH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[C:27]([CH:32]=O)[CH:26]=[CH:25]3)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12].ClCCCl.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:11]([CH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[C:27]([CH2:32][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[C:7]([OH:9])=[O:8])[CH:26]=[CH:25]3)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]

Komponenten

7

Edukt 6

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 849Pipecolic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866684126-(trans-4-Tert-butylcyclohexyloxy)-2-naphthaldehyde

Produkt 1

HCID 601631011-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-piperidine-2-carboxylic acidAusbeute 0,9 %

Versuchsvorschrift

Piperidine-2-carboxylic acid (0.125 g, 0.967 mmol) as HCl salt was combined with 6-(4-tert-Butyl-cyclohexyloxy)-naphthalene-2-carbaldehyde (0.250 g, 0.805 mmol) in 1,2-dichloroethane (5 mL, 60 mmol) and acetic acid (0.500 mL, 8.79 mmol). The mixture was heated to reflux while stirring overnight. Reaction cooled to room temperature and then sodium triacetoxyborohydride (546 mg, 2.58 mmol) was added in small portions. The reaction was then left stirring overnight. Reaction was then purified directly via reverse phase chromatography (5-95% CH3CN/Water (0.1% TFA), C18, 150 mm). The product was then lyophilized to dryness to give 3 mg 1-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-piperidine-2-carboxylic acid as a yellow solid (0.8%). ESI-LCMS (424 M+H). 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 12.34-12.58 (m, 1H), 11.20-11.53 (m, 1H), 8.01 (s, 1H), 7.68-7.93 (m, 3H), 7.41 (s, 1H), 7.02-7.22 (m, 1H), 4.35 (br. s., 3H), 3.23-3.43 (m, 2H), 2.86-3.09 (m, 2H), 1.74-2.30 (m, 8H), 1.00-1.52 (m, 5H), 0.87 (s, 9H)

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customReaction
  4. waitThe reaction was then left
  5. stirringstirring overnight
  6. customReaction
  7. customwas then purified directly via reverse phase chromatography (5-95% CH3CN/Water (0.1% TFA), C18, 150 mm)

Quellen und Nachweise

ORD-Eintrag
ord-82d73abbfad64d4b8cce4556d174ebc2
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340527B2

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