Nitrogen → HCID 54597212, compound

HRID 406131Notes

Reaction equation

HRID 406131 reaction equation
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:9][C@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C@H:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[O:28])=[CH:22][CH:21]=2)[CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].N#N>ClCCCl>[CH:1]1([CH2:6][N:33]2[CH2:34][CH2:35][CH:30]([NH:29][C:27](=[O:28])[CH2:26][C:23]3[CH:22]=[CH:21][C:20]([N:17]4[CH2:18][CH2:19][C@H:15]([N:11]5[CH2:12][CH2:13][CH2:14][C@@H:10]5[CH3:9])[CH2:16]4)=[CH:25][CH:24]=3)[CH2:31][CH2:32]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 70106CyclopentanecarbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71280830HCID 71280830, compound

Product 1

HCID 54597212HCID 54597212, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of cyclopentane-carboxaldehyde (138 mg, 1.4 mmol) and 2-[4-((2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-phenyl]-N-piperidin-4-yl-acetamide hydrochloride (0.52 g, 1.18 mmol) in DCE (10 mL) was added powder sodium triacetoxyborohydride slowly under N2 at r.t. The yellowish milky solution was stirred at r.t. overnight. LC/MS showed a major peak at 2.300 min with MS of 453. The reaction was quenched with NaHCO3 aq. (15 mL) and NaOH (1N, 5 mL). The two layers were separated, and the aqueous layer was extracted with DCM (10 mL×2). The combined DCM extracts were washed with sodium bicarbonate (10 mL), and brine (5 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo to get 0.30 g (56%) of the title compound as a tan solid.

Workup

  1. customat 2.300 min
  2. customThe reaction was quenched with NaHCO3 aq. (15 mL) and NaOH (1N, 5 mL)
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with DCM (10 mL×2)
  5. washThe combined DCM extracts were washed with sodium bicarbonate (10 mL), and brine (5 mL×2)
  6. dry with materialdried (anhydrous potassium carbonate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcab0ffb948248e1b9734777b88c6f00
Source dataset
uspto-grants-2014_06
Patent number
US08754095B2

Reaction notes

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