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

HRID 371161Notes

Reaction equation

HRID 371161 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5ca190d8b43f41a990e3b0ca03da0cbb
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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