methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(quinolin-6-yl)propanoate → methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1,2,3,4-tetrahydroquinolin-6-yl)propanoate

HRID 74817Notes

Reaction equation

HRID 74817 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86685771methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(quinolin-6-yl)propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 69563299methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1,2,3,4-tetrahydroquinolin-6-yl)propanoateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of #213 (1.5 g, 4.55 mmol, 1 eq.) and palladium on carbon (150 mg) in ethanol (20 mL) was stirred at 50° C. under 30 psi of hydrogen overnight. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The residue was purified by silica column chromatography (Gradient: 40% ethyl acetate in petroleum ether) to afford #214 (1.2 g, 80%) as an oil. 1H NMR (400 MHz, CDCl3): δ 6.70 (d, 2H), 6.40 (m, 1H), 4.95 (m, 1H), 4.49 (m, 1H), 3.77 (s, 3H), 3.28 (m, 2H), 2.97 (m, 2H), 2.71 (m, 2H), 1.95 (m, 2H), 1.26 (s, 9H), HPLC (Protocol Y): m/z 357.0 [M+Na+] retention time=5.304 minutes (purity >98%). Chiral HPLC retention time: 4.64 min (purity=98%)(Column: Chiralcel OJ-H, 150×4.6 mm, 5 μm; Mobile phase: ethanol (0.05% diethylamine) in CO2 from 5% to 40% over 15 minutes; Flow rate: 2.5 mL/minute.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica column chromatography (Gradient: 40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9af9013f680f4e40b8b77e774c015ad9
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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