Acetic Anhydride → HCID 90417394, compound

HRID 1484820Notes

Reaction equation

HRID 1484820 reaction equation
Cl.[C:2]1([C:8]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]=2[CH2:14][OH:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:25][C:26](OC(C)=O)=[O:27]>C(Cl)Cl.O>[OH:15][CH2:14][C:9]1[CH2:10][N:11]([C:26](=[O:27])[CH3:25])[CH2:12][CH2:13][C:8]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 90418087HCID 90418087, compound

Product 1

HCID 90417394HCID 90417394, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-phenyl-1,2,5,6-tetrahydropyridin-3-yl)methanol hydrochloride (110 mg, 0.49 mmol) in DCM (2 mL) was added DIPEA (0.17 mL, 0.98 mmol) and Ac2O (0.05 g, 0.49 mmol), 15 min later, it was diluted with water and extracted with DCM. Organic layers were combined, dried and concentrated, the resulting crude oil was purified by column (EtOAc followed by DCM/MeOH=9:1) to give 1-(5-(hydroxymethyl)-4-phenyl-3,6-dihydropyridin-1(2H)-yl)ethan-1-one (88 mg).

Workup

  1. extractionextracted with DCM
  2. customdried
  3. concentrationconcentrated
  4. customthe resulting crude oil was purified by column (EtOAc followed by DCM/MeOH=9:1)

Sources & evidence

ORD record
ord-3bd74e1327e448a0aa6f6d45ff67284f
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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