Hydrochloric Acid → 4-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxymethyl]piperidine-1-carboxylic acid benzyl ester

HRID 1711415Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:29][S:30]([C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31].CC(C)([O-])C.[K+].Cl>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([CH2:29][S:30]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)(=[O:31])=[O:32])[CH:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of 4-(4-nitrophenoxymethyl)piperidine-1-carboxylic acid benzyl ester (0.8 g, 2.16 mmoles) and 1-chloromethanesulfonylnaphthalene (1.03 g, 4.3 mmoles) in THF (50 ml) at −78° C., under nitrogen, was treated dropwise with a solution of 1M potassium t-butoxide (6.5 ml, 6.5 mmoles) over a 30 minute period, allowed to warm to −40° C., stirred at −40° C. for 5 hours, poured into cold 2N HCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4, and concentrated under vacuum. The resultant was purified by normal phase HPLC on a silica column, using as eluent 40% EtOAc/hexane, to afford the title compound as an off-white solid (0.9 g, 1.6 mmoles).

Workup

extractionextracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe resultant was purified by normal phase HPLC on a silica column

Sources & evidence

ORD record: ord-9ea5f8607bad450da54c543cba6e9390
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790751B2

Reaction notes

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