Acetaldehyde → HCID 86719534, compound

HRID 2208675Notes

Reaction equation

HRID 2208675 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]([CH3:22])=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.[CH:27](=O)[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]([CH3:22])=[C:6]([N:8]([CH2:27][CH3:28])[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70873837HCID 70873837, compound

Product 1

HCID 86719534HCID 86719534, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-{[5-chloro-3-(methoxycarbonyl)-2-methylphenyl]amino}piperidine-1-carboxylate (2.40 g, 6.28 mmol) in dichloromethane (50 mL) and acetic acid (1.8 mL) was added acetaldehyde (830 ul, 12.6 mmol) and sodium triacetoxyborohydride (4.00 g, 18.8 mmol). The reaction mixture was stirred at rt for 18 hours. Then aq. NaHCO3 was added and the mixture was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (SiO2 heptane/ethylacetate=10/1) to give the titled compound as oil (2.40 g, 89% yield). 1H-NMR (400 MHz, CDCl3) δppm; 7.56 (s, 1H), 7.21 (d, J=1.6 Hz, 1H), 4.04 (m, 2H), 3.89 (s, 3H), 3.02 (q, J=7.0 Hz, 2H), 2.88 (m, 1H), 2.68 (m, 2H), 2.44 (s, 3H), 1.71 (m, 2H), 1.48-1.61 (m, 2H), 1.45 (s, 9H), 0.83-0.89 (t, J=7.0 Hz, 3H); MS (ES) [M+Na] 433.0.

Workup

  1. customthe mixture was separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. concentrationThe combined organic layer was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (SiO2 heptane/ethylacetate=10/1)

Sources & evidence

ORD record
ord-6c2bd69326054ebfb063421b56695ed5
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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