Sodium borohydride → 6-hydroxymethyl-3-(4-trifluoromethyl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one

HRID 77362Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([CH:21]=[O:22])=[CH:19][CH:20]=[C:3]12.[BH4-].[Na+]>C(O)C.O1CCCC1>[OH:22][CH2:21][C:18]1[N:4]2[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][CH:9]=3)[NH:7][C:2](=[O:1])[C:3]2=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbaldehyde (0.02 g, 65.3 μmol) in ethanol (0.25 mL) and tetrahydrofuran (0.25 mL) cooled to 0° C. was treated with sodium borohydride (3 mg, 79.3 μmol). The reaction was stirred at 0° C. for 1 h and then was stored in the refrigerator overnight. At this time, the reaction was concentrated in vacuo. The remaining solid was triturated with water, collected by filtration, washed with water and dried in vacuo to afford 6-hydroxymethyl-3-(4-trifluoromethyl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one (10 mg, 50%) as an off-white solid. 1H NMR (DMSO-d6) δ ppm 7.87-7.96 (m, 3H), 7.79-7.87 (m, 2H), 7.40 (s, 1H), 6.87 (s, 1H), 5.03 (t, J=5.4 Hz, 1H), 4.50 (d, J=5.0 Hz, 2H). LC-MS calcd. for C15H12F3N2O2 [(M+H)+] 309, obsd. 309.0.

Workup

customwas stored in the refrigerator overnight
concentrationAt this time, the reaction was concentrated in vacuo
customThe remaining solid was triturated with water
filtrationcollected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-4284e1f3ff0b434592d9be81945c1a40
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841299B2

Reaction notes

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