Sodium borohydride → HCID 117739239, compound

HRID 1507163Notes

Reaction equation

FC(F)(F)C([N:5]([CH2:20][C:21]1[CH:26]=[C:25]([C:27](OCC)=[O:28])[CH:24]=[CH:23][N:22]=1)[CH2:6][C:7](=[O:19])[N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=O.[BH4-].[Na+]>>[OH:28][CH2:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([CH2:20][NH:5][CH2:6][C:7]([N:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:19])[CH:26]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 90375220HCID 90375220, compound

Product 1

HCID 117739239HCID 117739239, compound

Procedure

Prepared by General Procedure U from ethyl 2-[(2,2,2-trifluoro-N-{2-oxo-2-[(2R)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]ethyl}acetamido)methyl]pyridine-4-carboxylate, using 5 equiv. of NaBH4. The residue was purified by column chromatography on silica gel using NH4OH (2%)+MeOH (20%) in CH2Cl2 to give the title as yellow oil. 1H NMR (300 MHz, CD3OD), δ ppm: 8.44 (d, 1H), 7.49 (s, 1H), 7.31 (d, 1H), 4.90 (s, 2H), 4.69 (s, 2H), 4.24 (m, 1H), 3.93 (s, 2H), 3.50-3.36 (m, 3H), 2.67-2.42 (m, 6H), 2.06-1.89 (m, 4H), 1.84-1.72 (s, 4H). ESI-MS (m/z): 333 [M+1].

Workup

customThe residue was purified by column chromatography on silica gel
customto give the title as yellow oil

Sources & evidence

ORD record: ord-3a6e3930bb354e79a51619aa2225becb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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