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Methyl chloroformate → N-Methoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

HRID 371161
ノート
印刷プレビュー

反応式

HRID 371161 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:29][C@@H:28]([OH:30])[CH2:27][CH2:26][NH:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:39]([O:41][CH3:42])=[O:40]>O1CCCC1.CCOCC>[CH3:42][O:41][C:39]([N:25]1[CH2:26][CH2:27][C@H:28]([OH:30])[CH2:29][C@@H:24]1[C:10]1[CH:11]=[CH:12][C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6586Methyl chloroformate2 回HCID 8471TriethylamineHCID 70413103Cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

生成物 1

HCID 70413105N-Methoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol収率 89.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a 0° C. solution of 193 mg (0.471 mmole) of cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol and 0.29 ml triethylamine in 2.2 ml tetrahydrofuran is added dropwise 40 microliters (0.518 mmole) of methyl chloroformate. The reaction is stirred 40 minutes and then another 10 microliters of methyl chloroformate is added. The reaction is stirred 40 minutes longer, diluted with ether and filtered. The filtrate is washed with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The crude product is purified via column chromatography on 10.4 g of silica gel eluting in 3 ml fractions with 1:3 ethyl ether/hexane to yield (fractions 16-30) 198 mg (80%) of the title compound as an oil.

後処理

  1. stirringThe reaction is stirred 40 minutes longer
  2. filtrationfiltered
  3. washThe filtrate is washed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to an oil
  6. customThe crude product is purified via column chromatography on 10.4 g of silica gel eluting in 3 ml fractions with 1:3 ethyl ether/hexane

出典と根拠

ORDレコード
ord-5ca190d8b43f41a990e3b0ca03da0cbb
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04529732

反応ノート

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