Ammonium formate → HCID 22100044, compound

HRID 1457720Notes

Reaction equation

HRID 1457720 reaction equation
[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[S:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+].C([BH3-])#[N:20].[Na+]>CO.CCOC(C)=O>[CH3:13][O:12][C:10](=[S:11])[CH2:9][CH:8]([NH2:20])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydrideHCID 53682263HCID 53682263, compound

Product 1

HCID 22100044HCID 22100044, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl phenylthioacetoacetate (1.00 g, 4.5 mmol) in MeOH (20 ml), ammonium formate (4.26 g, 6.75 mmol) and sodium cyanoborohydride (0.42 g, 6.7 mmol) were added. The reaction mixture was stirred at room temperature for 18 h, then diluted with EtOAc and partitioned into 1M HCl. The aqueous layer was then basified to pH=8.0 with NaOH. The desired product was extracted out with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated to yield 0.61 g yellow oil; MS (NH3 -CI/DDIP) Calc. for (M+H)+ : 226. Found: 226; 1H NMR (300 MHz, CDCl3)δ 7.39 (d, J=7, 2H), 7.32-7.26 (m, 3H), 7.22 (d, J=10, 1H), 3.74 (s, 3H), 3.39-3.31 (m, 1H), 3.13-3.07 (dd, J=13, J'=9, 1H), 2.91-2.83 (dd, J=12, J'=6, 1H), 2.65-2.58 (dd, J=12, J'=6, 1H), 2.46-2.38 (dd, J=16, J'=8, 1H).

Workup

  1. custompartitioned into 1M HCl
  2. extractionThe desired product was extracted out with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23fcf297782c4dc7940052158690739a
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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