Potassium Acetate → HCID 66669427, compound

HRID 705654Notes

Reaction equation

HRID 705654 reaction equation
Cl[CH2:2][C@H:3]1[O:8][CH2:7][C@@H:6]2[CH2:9][CH2:10][CH2:11][N:5]2[CH2:4]1.[C:12]([O-:15])(=[O:14])[CH3:13].[K+]>CN(C)C=O>[C:12]([O:15][CH2:2][C@H:3]1[O:8][CH2:7][C@@H:6]2[CH2:9][CH2:10][CH2:11][N:5]2[CH2:4]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 53630913HCID 53630913, compound

Product 1

HCID 66669427HCID 66669427, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3S,8aS)-3-(Chloromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazine (2.30 g, 13.1 mmol) and potassium acetate (12.8 g, 131 mmol) were stirred in dimethylformamide (25 mL) at 140° C. for 20 h. The mixture was partitioned between ethyl acetate and water. The organic portion was washed twice with water, then with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford (3S,8aS)-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-ylmethyl acetate as a brown oil (2.53 g, 12.7 mmol, 97% yield). 1H NMR (400 MHz, CDCl3): 4.14-4.02 (m, 3H), 3.81-3.72 (m, 1H), 3.37-3.31 (m, 1H), 3.09 (dt, 1H), 3.00 (dd, 1H), 2.21-2.00 (m, 3H), 2.10 (s, 3H), 1.90-1.67 (m, 3H), 1.39-1.24 (m, 1H); MS (EI) for C10H17NO3: 200 (MH+).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic portion was washed twice with water
  3. dry with materialwith brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4459a4c3e9a746b4af03372bed74e85f
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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