Acetic Anhydride → HCID 21963936, compound

HRID 2212363Notes

Reaction equation

HRID 2212363 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CN(C1C=CC=CN=1)C>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:19](=[O:21])[CH3:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 21963936HCID 21963936, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-benzhydryl-azetidin-3-ol (3.56 g, 14.9 mmol.) in dichloromethane (60 mL) was added acetic anhydride (2.1 mL, 22.4 mmol.), triethylamine (3.1 mL, 22.4 mmol.) and dimethylaminopyridine (ca. 10 mg). The mixture was stirred for 3 hours then diluted with ethyl acetate (200 mL) and washed with saturated aqueous ammonium chloride solution (100 mL), 1N aqueous sodium hydroxide (100 mL) and brine (100 mL), dried (MgSO4) and evaporated to leave N-benzhydryl-3-acetoxy-azetidine (4.2 g) which was used without further purification.

Workup

  1. washwashed with saturated aqueous ammonium chloride solution (100 mL), 1N aqueous sodium hydroxide (100 mL) and brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-1cac987cd4b34efd854207f5ffebd83a
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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