Chloroform → HCID 136409724, compound

HRID 437065Notes

Reaction equation

HRID 437065 reaction equation
[NH2:1][C@H:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4].C(Cl)(Cl)Cl>[Cu].CO>[CH:3](=[N:1][C@H:2]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[OH:4])[C:5]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:11]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 22084864HCID 22084864, compound

Product 1

HCID 136409724HCID 136409724, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 0.43 g. (1.4 millimols) of bis (salicylaldehydate) copper in 10 ml. methanol was added dropwise a solution of 1.1 g. (3.0 millimols) of (R)-2-amino-1,1-di(2-methoxyphenyl)-3-phenyl-1-propanol {[α]D +42.3° (c 1.1, chloroform)} in 10 ml. of methanol. The addition was carried out under thorough stirring at room temperature. The period of the addition was one hour and the reaction mixture was stirred for another one hour. The resulting solids were collected by filtration, washed with methanol and dried under reduced pressure to give a mononuclear complex of (R)-N-salicylidene-2-amino-1,1-di(2-methoxyphenyl)-3-phenyl-1-propanol as grayish blue crystals. Yield, 0.75 g. (58%), [α]546, +860° (c 0.065, benzene), melting point: 205° - 206° C. (decomposed).

Workup

  1. additionTo a suspension of 0.43 g
  2. additionThe addition
  3. additionThe period of the addition
  4. stirringthe reaction mixture was stirred for another one hour
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with methanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-8c04607f57ed4f1bbc4ef956bb3bddbc
Source dataset
uspto-grants-1977_06
Patent number
US04029683

Reaction notes

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