Acetic Anhydride → HCID 67373504, compound

HRID 1971915Notes

Reaction equation

HRID 1971915 reaction equation
[OH:1][CH:2]1[CH2:8][C@H:7]2[N:9]([CH3:10])[CH:3]1[CH2:4][C:5](=[O:11])[CH2:6]2.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:10][N:9]1[CH:3]2[CH:2]([O:1][C:19](=[O:21])[CH3:20])[CH2:8][C@@H:7]1[CH2:6][C:5](=[O:11])[CH2:4]2

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67374564HCID 67374564, compound

Product 1

HCID 67373504HCID 67373504, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled, stirred solution of (R)-6-hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (4.08 mmol, 0.634 g), triethylamine (20.4 mmol, 2.86 mL), and DMAP (0.245 mmol, 0.03 g) in dry DCM (3.5 mL) was added acetic anhydride (6.12 mmol, 0.58 mL). The reaction mixture was allowed to come to room temperature and was stirred for 12 hours. The reaction was evaporated and the resulting residue was purified on a 12 g SiO2 cartridge using 0-3% (2N NH3 in MeOH) in DCM to give acetic acid (R)-8-methyl-3-oxo-8-aza-bicyclo[3.2.1]oct-6-yl ester.

Workup

  1. temperatureTo an ice bath cooled
  2. customto come to room temperature
  3. customThe reaction was evaporated
  4. customthe resulting residue was purified on a 12 g SiO2 cartridge

Sources & evidence

ORD record
ord-fe7aef41390649bb9b784c14999ab5fb
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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