Triethylamine → benzyl (2S,5S)-5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 81142Notes

Reaction equation

Cl.[CH3:2][C@@H:3]1[NH:8][CH2:7][C@@H:6]([OH:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:17](Cl)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C(Cl)Cl>[OH:9][C@@H:6]1[CH2:7][N:8]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C@@H:3]([CH3:2])[CH2:4][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ±trans-6-methylpiperidin-3-ol hydrochloride (14.0 g, 0.092 mol) in CH2Cl2 (150 mL) was cooled to 0° C. Triethylamine (51.5 mL, 0.369 mol) was added slowly. CbzCl (13.59 mL, 0.092 mol) was added dropwise, keeping the temperature below 20° C. The reaction was allowed to warm overnight to room temperature. The reaction was quenched by addition of water and diluted further with additional CH2Cl2. The layers were separated and the organics were dried over MgSO4 and concentrated. The crude material was purified by silica gel gradient chromatography (0-75% ethyl acetate in hexanes), providing ±Benzyl trans-5-hydroxy-2-methylpiperidine-1-carboxylate.

Workup

customthe temperature below 20° C
temperatureto warm overnight to room temperature
customThe reaction was quenched by addition of water
additiondiluted further with additional CH2Cl2
customThe layers were separated
dry with materialthe organics were dried over MgSO4
concentrationconcentrated
customThe crude material was purified by silica gel gradient chromatography (0-75% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-1ad6b0ce4a494ce6a01ce5b402ae415b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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