Benzyl Bromide → HCID 86690094, compound

HRID 520377Notes

Reaction equation

HRID 520377 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:9]=[C:10]1[CH2:19][C:12]2([CH2:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13]2)[CH2:11]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl.C(#N)C>[O:9]=[C:10]1[CH2:11][C:12]2([CH2:15][CH:14]([C:16]([O:18][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:17])[CH2:13]2)[CH2:19]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 336952306-Oxospiro[3.3]heptane-2-carboxylic acid

Product 1

HCID 86690094HCID 86690094, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of (bromomethyl)benzene (564 mg) in CHCl3 (1 mL) was added to a stirred solution of 6-oxospiro[3.3]heptane-2-carboxylic acid (462 mg) and DIPEA (0.576 mL) in acetonitrile (2 mL) and CHCl3 (2 mL) and the mixture was stirred at rt overnight. The reaction mixture was evaporated to dryness and then purified by silica gel FCC (1:1 DCM:hexanes) to afford benzyl 6-oxospiro[3.3]heptane-2-carboxylate as a clear oil.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by silica gel FCC (1:1 DCM:hexanes)

Sources & evidence

ORD record
ord-6ba32ce6867541d787fcc22a433c322f
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…