Formaldehyde → HCID 178499335, compound

HRID 244921Notes

Reaction equation

HRID 244921 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]([C:17]([C@H:19]1[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18])[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:4].C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[CH:8][C:9]=1[N:10]([C:17]([C@H:19]1[CH2:20][CH2:21][C@H:22]([CH3:25])[CH2:23][CH2:24]1)=[O:18])[CH:11]1[CH2:12][CH2:13][N:14]([CH3:34])[CH2:15][CH2:16]1)=[O:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 178499334HCID 178499334, compound

Product 1

HCID 178499335HCID 178499335, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the product from step V (5.340 g) in 1,2-dichloroethane (60 mL) is added formaldehyde (1.94 mL of 37% aqueous solution, 23.88 mmol), followed by sodium triacetoxyborohydride (2.403 g, 11.34 mmol) in portions over 20 min. The mixture is stirred at room temperature overnight, then water is added to the mixture, and it is extracted with CH2Cl2. Organic fraction is washed with aqueous NaHCO3 and brine, dried over Na2SO4, concentrated and purified by column chromatography on silica gel eluting with 0-10% of MeOH in CH2Cl2 to give 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-4-yl)-amino]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. extractionis extracted with CH2Cl2
  2. washOrganic fraction is washed with aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel eluting with 0-10% of MeOH in CH2Cl2

Sources & evidence

ORD record
ord-355273b0297242aca8fd1791a0f9f82b
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

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