Acetic Anhydride → HCID 68585430, compound

HRID 17496Notes

Reaction equation

HRID 17496 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:15]([O:19][C:20]([CH2:22][NH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:1]([N:26]1[CH2:27][CH2:28][CH:24]([NH:23][CH2:22][C:20]([O:19][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:21])[CH2:25]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57146008HCID 57146008, compound

Product 1

HCID 68585430HCID 68585430, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, acetic anhydride (707 μl, 7.49 mmol) and triethylamine (1.39 ml, 9.98 mmol) were added to a dichloromethane (25 ml) solution of 3-(tert-butoxycarbonylmethylamino)pyrrolidine (1.00 g, 4.99 mmol) with cooling with ice, followed by stirring at room temperature for 17 hours. The solvent was evaporated away under reduced pressure, then the resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate gave the entitled compound (1.10 g, 91%) as a pale yellow oil.

Workup

  1. temperaturewith cooling with ice
  2. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-cf494a17ae5a40bcaf2aad978fbe8769
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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