Sodium borohydride → Ethyl 3-(4-((3,3-dimethylcyclobutyl)(hydroxy)methyl)benzamido)propanoate

HRID 1892699Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask containing ethyl 3-(4-(3,3-dimethylcyclobutanecarbonyl)benzamido)propanoate (1.21 g, approximately 2.55 mmol pure) was added anhydrous methanol (18.3 mL). The solution was cooled to 0° C. and sodium borohydride (414 mg, 11.0 mmol) was added. After 15 min., the reaction was quenched with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give 1.10 g of crude material. Purification by silica gel flash chromatography (0-50% ethyl acetate in heptane) afforded impure ethyl 3-(4-((3,3-dimethylcyclobutyl)(hydroxy)methyl)benzamido)propanoate (750 mg, approximately 1.8 mmol pure) as an oil. MS (M+1): 334.3.

Workup

customthe reaction was quenched with saturated aqueous ammonium chloride
extractionextracted three times with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give 1.10 g of crude material
customPurification by silica gel flash chromatography (0-50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-e9b8e7baadc74144b9fb365fa159b8d6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507533B2

Reaction notes

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