NADPH → (3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol

https://huagongshe.com/reaction/1972416

Participants

Role	Name	HCID	Charge
Reactant	NADPH	HCID 5884	—
Reactant	HCID 66582486	HCID 66582486	—
Reactant	(3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol	HCID 66586151	—
Reactant	HCID 70655502	HCID 70655502	—
Product	(3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol	HCID 66586150	—

Reaction Steps

(3R)-1-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol; (3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol; (3R)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-pyrrolidinol. 1H NMR (400 MHz, DMSO-d6) δ 8.07-8.05 (m, 1H), 7.69-7.67 (m, 1H), 7.38-7.36 (d, J=9.1 Hz, 2H), 7.32-7.29 (m, 1H), 6.90-6.86 (d, J=9.1 Hz, 2H), 4.71-4.67 (m, 1H), 4.17-4.12 (m, 3H), 3.46-3.41 (m, 2H), 3.17-3.04 (m, 1H), 2.99-3.92 (m, 2H), 2.63-2.59 (m, 1H), 2.48-2.38 (m, 3H), 1.95-1.89 (m, 2H), 1.61 (s, 3H), 1.55-1.50 (m, 1H). m/z (ESI, +ve ion) 520.1 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=3.50 μM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431563B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-6e0ca9386a3f44be8cdf0bf70d1d78c2
Source note	uspto-grants-2013_04