Sodium triacetoxyborohydride → N-[2-({(3R)-1-[4-Hydroxy-4-(4-iodophenyl)cyclohexyl]pyrrolidin-3-yl}amino)-2 oxoethyl]-3-(trifluoromethyl)benzamide

To a solution of 4-hydroxy-4-(4-iodophenyl)cyclohexanone (624 mg, 2 mmol) in CH2Cl2 (10 mL) was added N-((3R)-pyrrolidin-3-ylcarbamoylmethyl)-3-trifluoromethylbenzamide (730 mg, 2 mmol) and then NaBH(OAc)3 (666 mg, 3 mmol). After stirred for 1 h, the reaction was quenched with 10% NaHCO3, and extracted with EtOAc. The organic extracts were combined, washed with saline solution, dried over sodium sulfate, concentrated in vacuo. The residue was chromatographed on silica gel, eluting with 1% NH4OH in ethyl acetate/methanol (100/0 to 10/90) to yield the major isomer (544 mg, 44.2%) and the minor isomer (446 mg, 36.3% yield). For the major isomer, LCMS: 615.2 (M+H+, 100%); 1H NMR: (CDCl3) δ 8.09, (s, 1H); 7.98, (d, 1H); 7.77, (d, 1H); 7.67, (d, 2H); 7.57, (t, 1H); 7.28, (d, 2H); 7.22, (t, 1H, NH); 6.44, (d, 1H, NH); 4.49, (m, 1H); 4.12, (m, 2H); 2.87, (m, 1H); 2.64, (m, 2H); 2.38, (m, 1H); 2.25, (m, 4H); 1.93, (m, 2H); 1.54-1.70, (m, 6H).

1. customthe reaction was quenched with 10% NaHCO3
2. extractionextracted with EtOAc
3. washwashed with saline solution
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was chromatographed on silica gel
7. washeluting with 1% NH4OH in ethyl acetate/methanol (100/0 to 10/90)
8. customto yield the major isomer (544 mg, 44.2%)

ORD 기록

ord-85239bb83b174ddb82319568f5850214

출처 데이터셋

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07985730B2