Sodium triacetoxyborohydride → HCID 59444140, compound

HRID 1969007Notes

Reaction equation

HRID 1969007 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][C:7]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)([CH3:10])[CH2:6][CH2:5]1)[CH3:2].[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][C:7]([N:11]2[CH2:16][CH2:15][CH:14]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13][CH2:12]2)([CH3:10])[CH2:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 59419744HCID 59419744, compoundHCID 59444053HCID 59444053, compound

Product 1

HCID 59444140HCID 59444140, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
140 °C

Procedure

1-[4-(Ethyloxy)-1-methylcyclohexyl]-4-piperidinone (D8) (0.350 g, 1.462 mmol)+ethyl (2E)-3-(2-amino-4-methylphenyl)-2-propenoate (D142) (0.1 g, 0.487 mmol) were placed in a microwave vial with 1,2-dichloroethane (DCE) (0.974 mL) and stirred for 10 mins. Sodium triacetoxyborohydride (0.387 g, 1.827 mmol) was added and the mixture heated at 140° C. for 10 mins. LCMS of the crude reaction mixture showed product (67% by u.v.). The reaction was quenched with NaHCO3 (10 mL, sat. aq) and then extracted with DCM (3×20 mL). The organic phases were combined, dried (phase sep. cartridge) and passed through a SCX-3 cartridge, eluting with DCM/MeOH to remove any neutral/acidic by-products. The product was eluted from the cartridge with 0.5 M NH3/MeOH to give a dark yellow oil. The crude product was purified by column chromatography using a 5 g cartridge and eluting with DCM-8% NH3/MeOH/DCM to give the product as a bright yellow/green oil (0.117 g, 56%).

Workup

  1. customLCMS of the crude reaction mixture
  2. customThe reaction was quenched with NaHCO3 (10 mL, sat. aq)
  3. extractionextracted with DCM (3×20 mL)
  4. customdried (phase sep. cartridge)
  5. washeluting with DCM/MeOH
  6. customto remove any neutral/acidic by-products
  7. washThe product was eluted from the cartridge with 0.5 M NH3/MeOH
  8. customto give a dark yellow oil
  9. customThe crude product was purified by column chromatography
  10. washeluting with DCM-8% NH3/MeOH/DCM

Sources & evidence

ORD record
ord-77dbc6762d9540ecb3ba4405489f99ea
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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