4-Cyanobenzaldehyde → Methyl 2-(4-cyanobenzyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

HRID 1773467Notes

Reaction equation

HRID 1773467 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=2)[CH2:19][CH2:18][NH:17]1.[C:30]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)#[N:31].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)C>[C:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:17]2[CH2:18][CH2:19][C:20]3[C:25](=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)[CH2:16]2)=[CH:34][CH:33]=1)#[N:31]

Participants

7

Reactant 4

HCID 660424-CyanobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 44607839Methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylate hydrochloride

Product 1

HCID 66897392Methyl 2-(4-cyanobenzyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (2.2 g, 10.4 mmol) was added to a solution of methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylate hydrochloride (1.0 g, 4.4 mmol) and 4-cyanobenzaldehyde (0.83 g, 6.3 mmol) in dichloromethane (10 mL). The resulting reaction mixture was allowed to stir at room temperature overnight, poured over saturated sodium bicarbonate solution (75 mL) and extracted with dichloromethane (3×30 mL). The combined organic layer was washed with water (2×30 mL), dried (MgSO4), filtered and concentrated to give a foamy residue. Column chromatography (30% ethyl acetate/hexanes) provided methyl 2-(4-cyanobenzyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate as a white crystalline solid upon trituration with ethyl ether (1.30 g, 97%). 1H NMR (CDCl3) δ 7.85 (1H, d, J=7.7 Hz); 7.72-7.58 (5H, m); 7.23 (1H, d, J=8.0 Hz); 4.00-3.98 (2H, m); 3.92 (3H, s); 3.83 (2H, br s); 3.08 (2H, br s); 2.97 (2H, br s). MS (M+H)+=307.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with dichloromethane (3×30 mL)
  3. washThe combined organic layer was washed with water (2×30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a foamy residue

Sources & evidence

ORD record
ord-ac8055983c7d464b90de16504d52b35d
Source dataset
uspto-grants-2016_02
Patent number
US09255085B2

Reaction notes

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