Benzyl chloroformate → HCID 178485997, compound

HRID 25653

Reaction equation

HRID 25653 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[N:2]([C@H:3]1[CH2:8][CH2:7][C@@H:6]([OH:9])[CH2:5][CH2:4]1)[CH3:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 178484842HCID 178484842, compound

Product 1

HCID 178485997HCID 178485997, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A well stirred solution of 100 g (774 mmol) of cis-4-Methylamino-cyclohexanol [Schut, Robert N. Analgesic 3-(methylamino)-1,2,3,4-tetrahydrocarbazole from 4-(methylamino)cyclohexanone. Fr. (1968), 3 pp. FR 1515629 19680301] in 775 ml EtOAc was treated with 1.55 l of aqueous 1M NaHCO3 and with 110 ml (774 mmol) of benzyl chloroformate (30 min, Tmax 30° C.). The phases were separated after 2 h at RT. The aqueous phase was extracted (EtOAc), the organic phases were dried (Na2SO4), filtered and evaporated. Purification by column chromatography on silica gel (hexane/EtOAc 2:1) gave 139 g (68%) of cis-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester, MS: 263 (M).

Workup

  1. customThe phases were separated after 2 h at RT
  2. extractionThe aqueous phase was extracted (EtOAc)
  3. dry with materialthe organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography on silica gel (hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-ba8db400e8fc435c9494ea1fa29d4128
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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