Hydroxyamine hydrochloride → 3,6-Diaza-bicyclo(3.2.0)heptane-6-carboxylic acid tert-butyl ester

HRID 1193072Notes

Reaction equation

HRID 1193072 reaction equation
C(OC(=O)[N:10]([CH2:15][CH:16]=[CH2:17])[CH2:11][CH:12]=[N:13]O)C1C=CC=CC=1.[CH2:19](OC(=O)N(CC=C)CC=O)[C:20]1[CH:25]=CC=C[CH:21]=1.Cl.NO.O.O.O.[C:42]([O-:45])(=[O:44])C.[Na+]>C(#N)C.O>[C:20]([O:45][C:42]([N:13]1[CH2:17][CH:16]2[CH:12]1[CH2:11][NH:10][CH2:15]2)=[O:44])([CH3:25])([CH3:21])[CH3:19]

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 57415664Benzyl allyl(2-oxoethyl)carbamateHCID 74074414Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamate

Product 1

HCID 467381813,6-Diaza-bicyclo(3.2.0)heptane-6-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Allyl-(2-hydroxyimino-ethyl)-carbamic acid benzyl ester. To a 1 L round-bottomed flask, were added allyl-(2-oxo-ethyl)-carbamic acid benzyl ester (45.2 g, 193.8 mmol) and hydroxylamine hydrochloride (17.5 g, 251.9 mmol) in acetonitrile (260 mL). To the resulting mixture was added a solution of sodium acetate trihydrate (29.5 g, 217 mmol) in H2O (130 mL). The reaction mixture was stirred at room temperature under nitrogen(g) overnight. The mixture was concentrated under reduced pressure and the resulting residue was extracted with ethyl acetate (2×130 mL). The combined organics were washed with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (46.5 g, 97%). 1H-NMR (CDCl3, 400 MHz): 7.32 (m, 5H), 6.72 (m, 1H), 5.77 (bs, 1H), 5.16 (m, 4H), 4.19 (m, 1H), 3.95 (m, 3H). MS (electrospray): exact mass calculated for C13H16N2O3, 248.12; m/z found, 249.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate (2×130 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9907532775db487789451489668292f8
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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