Sodium borohydride → HCID 178499282, compound

HRID 73182Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:18]([CH:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

3-[(4-Methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (55 mg, 0.121 mmol) was dissolved in methanol (1.2 ml), cooled to 0° C. and then sodium borohydride (4.6 mg, 0.121 mmol) was added. After 30 minutes of stirring at 0° C., the reaction was quenched with a 10% solution of hydrochloric acid (5 ml) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined ethyl acetate layer was dried (Na2SO4) and concentrated. The residue was then purified by preparative chromatography (3% MeOH/CH2Cl2) to obtain 34 mg (62%) of 3-[(trans-4-Hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Workup

customthe reaction was quenched with a 10% solution of hydrochloric acid (5 ml)
extractionthe aqueous phase was extracted with ethyl acetate (3×10 mL)
dry with materialThe combined ethyl acetate layer was dried (Na2SO4)
concentrationconcentrated
customThe residue was then purified by preparative chromatography (3% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-5365083db3df460099177d8d238f67a3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829030B2

Reaction notes

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