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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1293231Generated: October 31, 2026

Dimethylformamide → HCID 59462304, compound

https://huagongshe.com/reaction/1293231

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamateHCID 56973617—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
SolventDiethyl EtherHCID 3283—
ProductHCID 59462304HCID 5946230490%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of tert-butyl [(1S)-1-(4-bromophenyl)ethyl]carbamate (step 1 of Example 5, 1.50 g, 5.00 mmol), tetrakis(triphenylphosphine)palladium (0) (0.58 g, 0.50 mmol), zinc cyanide (0.59 g, 5.00 mmol) and N,N-dimethylforamide (30 mL) was stirred at 80° C. for 16 h under nitrogen atmosphere. After cooling to room temperature, the mixture was diluted with ether (200 mL) and washed with water (100 mL×3). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (4:1) to afford 1.11 g (90%) of the title compounds as colorless syrup: 1H-NMR (CDCl3) δ 7.64–7.61 (2H, m), 7.41 (2H, d, J=8.3 Hz), 4.83 (2H, br.s), 1.44–1.42 (12H, m).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07238714B2
Source datasetuspto-grants-2007_07
ORD IDord-e6d0305f05854781ace83cb7f372cc37
Source noteuspto-grants-2007_07