Dicyclohexylcarbodiimide → HCID 69583843, compound

HRID 1793760Notes

Reaction equation

HRID 1793760 reaction equation
[CH2:1]=[CH:2][C@@H:3]1[C@@H:8]2[CH2:9][C@@H:10]([C@H:11]([OH:22])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.[CH2:23]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:23]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([O:22][C@H:11]([C:12]2[C:17]3[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[CH:14][CH:13]=2)[C@@H:10]2[CH2:9][C@@H:8]3[CH2:7][CH2:6][N:5]2[CH2:4][C@@H:3]3[CH:2]=[CH2:1])=[O:35])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 708344-(Hexyloxy)benzoic acidHCID 101744Cinchonidine

Product 1

HCID 69583843HCID 69583843, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 9 was performed as Example 1 except for substitution of 2.91 g of cinchonidine, 2.0 g of 4-n-hexyloxy-benzoic acid, 2.33 g of N,N′-Dicyclohexyl carbodimide (DCC), 1.32 g of N,N-(dimethyl amino)-pyridine (DMAP) and 80 ml of dichloromethane into a round-bottom flask. After filtering and condensing, the residue was subjected to recrystallization from methanol, giving (R)-1-(4-quinolyl)-1-[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methyl 4-(hexyloxy)benzoate, as a white solid having a melting point about 70° C. in a 72.3% yield. The optical properties of the resulting compound were tested as in Example 1. The compound exhibited a specific rotation [α] of +57.59 and a helical pitch P of 5.1 μm, with helical twisting power of 19.7 μm−1.

Workup

  1. filtrationAfter filtering
  2. customcondensing
  3. customthe residue was subjected to recrystallization from methanol

Sources & evidence

ORD record
ord-87f53d684b364cf09e53e14f9aac66d6
Source dataset
uspto-grants-2006_04
Patent number
US07022259B2

Reaction notes

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