Ethyl Acetate → 4-(2-Bromo-5-methoxybenzyl)-1-Boc-piperidine

HRID 1006055Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[Br:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[C].[Rh].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[Br:23])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of N-tert-butoxycarbonyl-4-(2-bromo-5-methoxybenzal)piperidine (87.7 g, 0.229 mol), 5% rhodium-carbon (25.6 g), ethyl acetate (150 mL) and ethyl alcohol (150 mL) was stirred at 40° C. for 16 hours under a hydrogen atmosphere. The precipitate was filtered and then washed with ethyl acetate, and the filtrate was concentrated to dryness. The residue was diluted with ethyl acetate (800 mL) and washed with a saturated aqueous sodium chloride solution (100 mL). The dilution was dried over anhydrous magnesium sulfate and then concentrated to dryness to obtain 78.7 g (0.205 mol, 89%) of N-tert-butoxycarbonyl-4-(2-bromo-5-methoxybenzyl)piperidine.

Workup

filtrationThe precipitate was filtered
washwashed with ethyl acetate
concentrationthe filtrate was concentrated to dryness
additionThe residue was diluted with ethyl acetate (800 mL)
washwashed with a saturated aqueous sodium chloride solution (100 mL)
dry with materialThe dilution was dried over anhydrous magnesium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-5ca5df67be42400bb133e02020173af5
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787560B2

Reaction notes

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