Nitrogen → 3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide

HRID 1503260Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18](OC)=[O:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].[Li+].[BH4-].N#N>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][C:10]([CH2:18][OH:19])([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 3-[(3-chlorobenzoyl)amino]adamantane-1-carboxylate (220 mg, 0.63 mmol) in THF (15 mL) at 0° C. was added LiBH4 (2.0M in THF, 0.6 mL, 1.2 mmol) dropwise under N2. After stirring at 0° C. for 30 min, the reaction mixture was allowed to warm up to room temperature overnight. The reaction was quenched with Sat. NH4Cl, and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 200 mg (99%) of the title compound, 3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide, as a colorless oil, which was used in the next step without further purification. ESI-MS m/z: 320 (M+H)+.

Workup

temperatureto warm up to room temperature overnight
customThe reaction was quenched with Sat. NH4Cl
extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
washThe combined organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a5787bddac0b4c52b2a511c24e1d6a2d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212165B2

Reaction notes

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