Sodium Carbonate → HCID 71145212, compound

HRID 535325Notes

Reaction equation

HRID 535325 reaction equation
Cl.[CH:2]12[C:10](=[O:11])[CH:6]([CH2:7][NH:8][CH2:9]1)[CH2:5][O:4][CH2:3]2.C([O-])([O-])=O.[Na+].[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CCOC(C)=O>[CH2:22]([O:21][C:19]([N:8]1[CH2:7][CH:6]2[C:10](=[O:11])[CH:2]([CH2:3][O:4][CH2:5]2)[CH2:9]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 71650382HCID 71650382, compound

Product 1

HCID 71145212HCID 71145212, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 3-oxa-7-aza-bicyclo[3.3.1]nonan-9-one hydrochloride [CAS #1228600-54-1] (4.80 g, 27 mmol), EtOAc (105 ml) and saturated aqueous Na2CO3 (105 ml) was added benzyl chloroformate (4.60 ml, 32.4 ml) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then extracted with EtOAc (2×). The organic phases were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by normal phase column chromatography, eluting with heptane-EtOAc 1:1, gave the title compound as a colorless oil (5.75 g, 20.68 mmol, 77%): 1H-NMR (400 MHz, DMSO-d6): δ 2.31-2.35 (d, 2H), 2.34 dd, 2H), 3.78 (d, 2H), 4.19 (t, 2H), 4.55 (q, 2H), 5.11 (m, 2H), 7.28-7.38 (m, 5H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by normal phase column chromatography
  7. washeluting with heptane-EtOAc 1:1

Sources & evidence

ORD record
ord-b77eb7b0a8324a62939d8ae9bcf0ca60
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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