Triethylamine → HCID 13294373, compound

HRID 1379124Notes

Reaction equation

HRID 1379124 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH:4]=[CH:3]1.[CH2:9]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C=O)C.CCOCC>[OH:8][CH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH:3]=[CH:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 12651624HCID 12651624, compound

Product 1

HCID 13294373HCID 13294373, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.64 g of cis-4-amino-2-cyclohexen-1-ol, 10.2 g of N-(benzyloxycarbonyloxy)succinimide and 5.7 ml of triethylamine in DMF is diluted with ether after stirring, washed with saturated sodium chloride solution, dried and concentrated. Chromatography of the residue on silica gel (ethyl acetate/hexane 2:1) gives 5.62 g of benzyl (1RS,4SR)-4-hydroxy-2-cyclohexene-1-carbamate. MS: 156 (M+H)+.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5394a7fab6084531a8f39b8f3b34eb5e
Source dataset
uspto-grants-1997_09
Patent number
US05670515

Reaction notes

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