tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → HCID 21959486, compound

HRID 2356966Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28]Br)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CC(C)([O-])C.[K+]>CN(C)C=O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=3)[C:2]([CH3:14])([CH3:1])[CH2:3]2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A process vial with a suspension of 1 g 3,3-dimethyl-6-nitro-2,3-dihydro-1H-indole, 1.59 g 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester and 1.17 g potassium tert-butoxide in 10 ml N,N-dimethylformamide was sealed with a teflon septum and placed in the microwave cavity. The reaction mixture was stirred for 15 minutes at 100° C. by microwave-assisted heating (Emrys Optimizer, Personal Chemistry). After removal of the solvent under reduced pressure the residue was purified by flash chromatography on silica gel with a n-heptane/ethylacetate gradient. The fractions containing the product were combined and evaporated to yield a white solid.

Workup

temperatureby microwave-assisted heating (Emrys Optimizer, Personal Chemistry)
customAfter removal of the solvent under reduced pressure the residue
customwas purified by flash chromatography on silica gel with a n-heptane/ethylacetate gradient
additionThe fractions containing the product
customevaporated
customto yield a white solid

Sources & evidence

ORD record: ord-03e4597ed6ec44969cfa1d297ebe0403
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759379B2

Reaction notes

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