Ammonia → 4-Ethynyl4-hydroxy-tetrahydro-pyran-2-carboxylic Acid Amide

HRID 1264042Notes

Reaction equation

HRID 1264042 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][C:10]([OH:18])([C:12]#[C:13][Si](C)(C)C)[CH2:9][CH2:8][O:7]1)=O)C.[NH3:19]>CO>[C:12]([C:10]1([OH:18])[CH2:9][CH2:8][O:7][CH:6]([C:4]([NH2:19])=[O:3])[CH2:11]1)#[CH:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 536671564-Hydroxy-4-trimethylsilanylethynyl-tetrahydro-pyran-2-carboxylic Acid Ethyl Ester

Product 1

HCID 536340094-Ethynyl4-hydroxy-tetrahydro-pyran-2-carboxylic Acid AmideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-4-trimethylsilanylethynyl-tetrahydro-pyran-2-carboxylic acid ethyl ester (2.50 g, 9.25 mmol) was dissolved in MeOH (20 mL) in a pressure reaction tube and NH3 gas was passed through the solution for 10 minutes with stirring. The tube was tightly capped and the reaction was stirred for 3 days. After solvent removal, 1.53 g (97%) of yellow oil was obtained: 1H NMR (CD3OD) δ 1.48 (t, 1H), 1.70 (td, 1H), 1.85 (d, 1H), 2.30 (d, 1H), 3.04 (s, 1H), 3.29 (s, 1H), 3.71(t, 1H), 3.98 (d, 1H), 4.06 (dt, 1H).

Workup

  1. customThe tube was tightly capped
  2. stirringthe reaction was stirred for 3 days
  3. customAfter solvent removal

Sources & evidence

ORD record
ord-051e03b2b4144d0b944c686fa79f8690
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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