Sodium borohydride → HCID 178495824, compound

HRID 1470009Notes

Reaction equation

[CH:1]([C:3]1[N:4]([CH2:21][CH2:22][O:23][CH3:24])/[C:5](=[N:9]/[C:10]([C:12]23[CH2:19][CH:18]4[CH2:20][CH:14]([CH2:15][CH:16]2[CH2:17]4)[CH2:13]3)=[O:11])/[S:6][C:7]=1[CH3:8])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH2:21][CH2:22][O:23][CH3:24])/[C:5](=[N:9]/[C:10]([C:12]23[CH2:19][CH:18]4[CH2:20][CH:14]([CH2:15][CH:16]2[CH2:17]4)[CH2:13]3)=[O:11])/[S:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of Example 127 (47.0 mg, 0.14 mmol) in methanol (3 mL) was added a solution of sodium borohydride (6.0 mg, 0.15 mmol) in methanol (3 mL). The reaction mixture was stirred at 0° C. for 30 minutes and then warmed to reflux for 1 hour. The reaction mixture was then cooled, quenched with aqueous 1 M aqueous HCl, neutralized with saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.48-1.65 (m, 4H), 1.66-1.82 (m, 4H), 2.08 (s, 1H), 2.12 (s, 1H), 2.23 (s, 3H), 2.26 (s, 2H), 2.52-2.59 (m, 1H), 3.24 (s, 3H), 3.66 (t, J=5.6 Hz, 2H), 4.34 (t, J=5.8 Hz, 2H), 4.46 (d, J=4.4 Hz, 2H), 5.29 (t, 1H); MS (ESI+) m/z 351 (M+H)+.

Workup

temperaturewarmed
temperatureto reflux for 1 hour
temperatureThe reaction mixture was then cooled
customquenched with aqueous 1 M aqueous HCl
extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-56e990fb4da14295b6e8cdc52ec952af
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006275B2

Reaction notes

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