Dicyclohexylcarbodiimide → (RS)-1-cyano-1-(6-phenoxypyrid-2-yl)methyl (1RS, trans)-3-(2-cyclohexylpyrimidine-5-yl)-2,2-dimethylcyclopropane carboxylate

HRID 845840Notes

Reaction equation

HRID 845840 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([C:22]2[N:27]=[CH:26][C:25]([C@H:28]3[C@H:30]([C:31]([O-:33])=[O:32])[C:29]3([CH3:35])[CH3:34])=[CH:24][N:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[C:36]([CH:38]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:41]=1)O)#[N:37]>CN(C)C1C=CN=CC=1.ClCCl>[CH:16]1([C:22]2[N:27]=[CH:26][C:25]([C@H:28]3[C@H:30]([C:31]([O:33][CH:38]([C:36]#[N:37])[C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([O:46][C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[N:41]=4)=[O:32])[C:29]3([CH3:35])[CH3:34])=[CH:24][N:23]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12884337Cyano(6-phenoxy-2-pyridyl)methanolHCID 86741457(+/-)-trans-3-(2-Cyclohexylpyrimidin-5-yl)-2,2-dimethylcyclopropane carboxylate

Product 1

HCID 86741456(RS)-1-cyano-1-(6-phenoxypyrid-2-yl)methyl (1RS, trans)-3-(2-cyclohexylpyrimidine-5-yl)-2,2-dimethylcyclopropane carboxylateYield 93.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dicyclohexylcarbodimide (118 mg) was added to a stirred mixture of (±)-trans-3-(2-cyclohexylpyrimidin-5-yl)-2,2-dimethylcyclopropane carboxylate (150 mg), 1-cyano-1-(6-phenoxypyrid-2-yl)methanol (130 mg), 4-dimethylaminopyridine (5 mg) and dichloromethane (5 cm3) and the mixture stirred at the ambient temperature for 7 hours, and kept for a further 16 hours without stirring. The product was isolated by filtering through a silica column, eluting first with dichloromethane and then with a mixture of dichloromethane (20 parts by volume) and ethyl acetate (1 part by volume) to yield (RS)-1-cyano-1-(6-phenoxypyrid-2-yl)methyl (1RS, trans)-3-(2-cyclohexylpyrimidine-5-yl)-2,2-dimethylcyclopropane carboxylate, (248 mg) identified by n.m.r. as a 1:1 mixture of the two pairs of enantiomeric diastereomers.

Workup

  1. waitkept for a further 16 hours
  2. stirringwithout stirring
  3. customThe product was isolated
  4. filtrationby filtering through a silica column
  5. washeluting first with dichloromethane
  6. additionwith a mixture of dichloromethane (20 parts by volume) and ethyl acetate (1 part by volume)

Sources & evidence

ORD record
ord-d597b9895c864fd8889880f30c2e73f8
Source dataset
uspto-grants-1988_07
Patent number
US04760143

Reaction notes

Loading…