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

HRID 1711415
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HRID 1711415 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 199924221-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 588286324-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxymethyl]piperidine-1-carboxylic acid benzyl ester수율 74.1%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9ea5f8607bad450da54c543cba6e9390
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790751B2

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