1-Chloroethyl chloroformate → HCID 58494064, compound

HRID 1942695Notes

Reaction equation

HRID 1942695 reaction equation
C([N:14]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([B:24]3[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]3)[C:19]=2[CH2:33][CH3:34])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>>[CH2:33]([C:19]1[C:20]([B:24]2[O:25][C:26]([CH3:31])([CH3:32])[C:27]([CH3:29])([CH3:30])[O:28]2)=[CH:21][CH:22]=[CH:23][C:18]=1[CH:16]1[CH2:17][NH:14][CH2:15]1)[CH3:34]

Participants

3

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58494046HCID 58494046, compound

Product 1

HCID 58494064HCID 58494064, compoundYield 14.2%

Procedure

To a solution of 1-Benzhydryl-3-[2-ethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-azetidine (D130) (3.4 g, 7.489 mmol) in 80 mL of 1,2-dicholoroethane was added proton sponges (200 mg, 0.933 mmol) and 1-chloroethyl chloroformate. The reaction mixture was refluxed for 10 hr, and then filtered. The filtrate was concentrated under reduced pressure to give the crude product, which was purified by Mass Directed AutoPrep to afford 3-[2-ethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-azetidine (D131) (305 mg). δH (DMSO-d6, 400 MHz): 0.98 (3H, t), 1.25 (12H, s), 2.72 (2H, q), 4.10 (2H, m), 4.24 (2H, m), 4.33 (1H, m), 7.23 (1H, m), 7.55 (2H, m), 9.0 (1H, br, s).

Workup

  1. temperatureThe reaction mixture was refluxed for 10 hr
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give the crude product, which
  5. customwas purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-d1d52717b314460aaefa4bfafe79c282
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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