Triethylamine → HCID 68490368, compound

HRID 453903Notes

Reaction equation

HRID 453903 reaction equation
Cl.Cl.[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.O=[C:28]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH2:16][N:15]([CH:32]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31]2)[CH2:14][CH2:13]3)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68423460HCID 68423460, compound

Product 1

HCID 68490368HCID 68490368, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-(Piperidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline dihydrochloride (0.5 g, 1.65 mmol), triethylamine (0.57 ml, 4.12 mmol) and tert-butyl 3-oxopyrrolidine-1-carboxylate (305 mg, 1.65 mmol) were dissolved in 1,2-dichloroethane (13 ml), and sodium triacetoxyborohydride (480 mg, 2.309 mmol) was added. The reaction mixture was stirred for 2 h, and then sat. sodium hydrogen carbonate solution was added. After phase separation, the aqueous phase was extracted with dichloromethane (2×). The combined organic phases were washed with sat. sodium chloride solution (1×), dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/ammonia (25% aq.) (200:20:1). Yield: 0.55 g (83%)

Workup

  1. customAfter phase separation
  2. extractionthe aqueous phase was extracted with dichloromethane (2×)
  3. washThe combined organic phases were washed with sat. sodium chloride solution (1×)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/ammonia (25% aq.) (200:20:1)

Sources & evidence

ORD record
ord-6c3e7824398f4ead91d3f679126891e8
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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