Triphenylphosphine → 7-[2-(1-tert-Butoxycarbonyl-4-cyanopiperidin-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester

HRID 412585Notes

Reaction equation

HRID 412585 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([OH:21])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][C:32]([C:38]#[N:39])([CH2:35][CH2:36]O)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:36][CH2:35][C:32]3([C:38]#[N:39])[CH2:33][CH2:34][N:29]([C:27]([O:26][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:28])[CH2:30][CH2:31]3)=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11254587Benzyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 60064207Tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 600641057-[2-(1-tert-Butoxycarbonyl-4-cyanopiperidin-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl esterYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (1.1 g), 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester (1 g) and triphenylphosphine (1.22 g) in tetrahydrofuran (40 ml) was added diethyl azodicarboxylate (2 g) with ice-cooling, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) and dried under reduced pressure to give the title compound (1.6 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-198b4ee417c64545b3c8b006040f8976
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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