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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1622183Generated: October 31, 2026

Chloroform → N-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

https://huagongshe.com/reaction/1622183

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroformHCID 6212—
ReactantAmmonium ChlorideHCID 25517—
ReactantLithium borohydrideHCID 4148881—
ReactantN-[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamideHCID 58973534—
SolventTetrahydrofuranHCID 8028—
ProductN-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamideHCID 5897348749.2%

Reaction Steps

In 1 ml of THF was dissolved 31.9 mg of N—[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide, 3.0 mg of lithium borohydride was added thereto, and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and chloroform was added to the mixture and the mixture was stirred and then the liquids were separated. The organic layer was dried and evaporated, and then, the residue was purified by NH silica gel thin-layer chromatography (chloroform:methanol=95:5) to obtain 14.7 mg of N—[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide (the following Table X, Example 12.003).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778628B2
Source datasetuspto-grants-2014_07
ORD IDord-fe85e07e9fab42f6bae25d6f4c07e7d0
Source noteuspto-grants-2014_07