Acetic Acid → HCID 86635665, compound

HRID 2388677Notes

Reaction equation

HRID 2388677 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([CH:17]=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[N:19]1([CH2:17][C:15]2[S:14][C:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]=3[CH:16]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 11845085tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

Product 1

HCID 86635665HCID 86635665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbalde-hyde (440 mg, 1.65 mmol) and piperidine (0.18 ml, 1.81 mmol) were dissolved in THF (10 ml), and NaBH(OAc)3 (523 mg, 2.47 mmol) and glacial acetic acid (94 μl, 1.65 mmol) were added. This mixture was stirred under a nitrogen atmosphere at room temperature for 24 hours. The solvent was then distilled off in vacuo and the residue was taken up in ethyl acetate (25 ml). The solution obtained was washed with NaHCO3 solution and NaCl solution and the combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The crude product (580 mg) was employed directly in the next stage without further purification.

Workup

  1. distillationThe solvent was then distilled off in vacuo
  2. customThe solution obtained
  3. washwas washed with NaHCO3 solution and NaCl solution
  4. dry with materialthe combined organic phases were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product (580 mg) was employed directly in the next stage without further purification

Sources & evidence

ORD record
ord-9da13eaea69e4af3a02f029d29b7fe50
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…