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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1806393Generated: November 2, 2026

Sodium triacetoxyborohydride → HCID 42629294, compound

https://huagongshe.com/reaction/1806393

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant(2S)-1,2-dimethylpyrrolidineHCID 11434918—
Reactant3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamideHCID 57732703—
CatalystAcetic AcidHCID 176—
SolventDimethyl SulfoxideHCID 679—
ProductHCID 42629294HCID 4262929417.3%

Reaction Steps

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (600 mg, 1.348 mmol) in dimethyl sulfoxide (10 mL) was added of 20 drops of acetic acid and (2S)-1,2-dimethylpyrrolidine (1.37 mL, 13.483 mmol). The resulting mixture was stirred at room temperature for 6 h followed by an addition of sodium triacetoxyborohydride (2.858 g, 13.483 mmol). The reaction was stirred at room temperature overnight then purified by SFC. This compound was separated by RTP CASS Group. The fraction of enantiomer #1 is 99.7% chirally pure to give 119.9 mg of the title compound (17.3%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354406B2
Source datasetuspto-grants-2013_01
ORD IDord-708326e1c89a40e08058fe6eb01b98b7
Source noteuspto-grants-2013_01