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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1666008Generated: October 31, 2026

Water → HCID 67357362, compound

https://huagongshe.com/reaction/1666008

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDiethyl chlorophosphateHCID 13139—
ReactantLithium HexamethyldisilazideHCID 2733832—
ReactantHCID 67356870HCID 67356870—
SolventTetrahydrofuranHCID 8028—
ProductHCID 67357362HCID 6735736210.7%

Reaction Steps

3-{t-Butyl[(2S)-2-(4-chlorophenyl)-2-hydroxyethyl]-amino}propanenitrile (5 g, 17.80 mmol) prepared according to the process described in WO 2004/09126 was dissolved in THF (27 mL). The reaction mixture was cooled to −20° C. or less, to which was added chlorodiethylphosphate (2.69 ml, 18.70 mmol). The reaction temperature was maintained at 12˜18° C., during which 1M LHMDS (37.4 ml, 37.38 mmol) was added dropwise over 2 hours. After the reaction was completed, water (45 mL) was added while the temperature was maintained at 15° C. or less. The resulting mixture was stirred for 30 minutes and extracted with EtOAc. Thus extracted organic solution was concentrated in vacuo and purified by column chromatography (eluent: EtOAc/Hex=1/3) to give the title compound (0.5 g, 10.69%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08039622B2
Source datasetuspto-grants-2011_10
ORD IDord-2ddddf9439844892a95c967f6a95d5cd
Source noteuspto-grants-2011_10