Triethylamine → trans-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidine-1-carboxylic acid t-butyl ester

HRID 1809062Notes

Reaction equation

HRID 1809062 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19](O)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH:29]1[C@H:38]2[C@@H:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:32][CH2:31][CH2:30]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:29]3[C@H:38]4[C@@H:33]([CH2:34][CH2:35][CH2:36][CH2:37]4)[CH2:32][CH2:31][CH2:30]3)=[O:20])[CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6994352(4aS,8aR)-DecahydroquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595424805-(1-(Tert-butoxycarbonyl)piperidin-4-yl)thiophene-3-carboxylic acid

Product 1

HCID 86646699trans-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidine-1-carboxylic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Carboxy-thiophen-2-yl)-piperidine-1-carboxylic acid t-butyl ester (0.1 g, 0.32 mmol) was dissolved in acetonitrile (2 mL). Triethylamine (0.96 mmol), trans-decahydroquinoline (1:1 mixture of the trans-isomers; 0.35 mmol) and HATU (0.35 mmol) were added and the reaction stirred at room temperature for 5 hours. The solvent was evaporated and the residue was purified by HPLC, eluting with 10%-90% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.09 g). 1H NMR (400 MHz, CHCl3-d): δ 7.2 (s, 1H), 6.9 (s, 1H), 4.2 (m, 2H), 3.7 (m, 1H), 3.5-3.3 (m, 2H), 3.0-2.7 (m, 3H), 2.25 (m, 1H), 2.0 (m, 2H), 1.8-1.5 (m, 8H) 1.5 (s, 9H), 1.4-1.0 (m, 6H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by HPLC
  3. washeluting with 10%-90% acetonitrile in water (0.1% formic acid)
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-e6daa23e317a4ee6952ab946e00e67b1
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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