Triphenylphosphine → HCID 56656612, compound

HRID 1636750Notes

Reaction equation

HRID 1636750 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[O:28])=[CH:23][CH:22]=1.[CH:36]1([N:39]([CH2:41][CH:42]2[CH2:44][CH:43]2[CH2:45]O)[CH3:40])[CH2:38][CH2:37]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:45][CH:43]3[CH2:44][CH:42]3[CH2:41][N:39]([CH:36]3[CH2:38][CH2:37]3)[CH3:40])=[CH:31][CH:30]=2)=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanoneHCID 70162160HCID 70162160, compound

Product 1

HCID 56656612HCID 56656612, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.2 g of triphenylphosphine, 6.5 g of (4-bromo-phenyl)-(4-hydroxy-phenyl)-methanone and 3.64 g of (1RS,2RS)-[2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropyl]-methanol (Ex. 31.1.A.d) in 190 ml of THF is treated at room temperature during 1 hr. with 4.03 ml of diethyl azodicarboxylate in 18 ml of THF. After stirring for 3 hrs. the mixture is concentrated, taken up in ether and washed with saturated sodium bicarbonate solution and 10% sodium chloride solution, dried and concentrated. The residue is dissolved in ether and precipitated with hexane. The mother liquor is concentrated and the crude (1RS,2RS)-(4-bromo-phenyl)-[4-[2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy]-phenyl]-methanone is dissolved in ethanol, treated with 2.7 g of fumaric acid and crystallized out. There are obtained 4.1 g of (1RS,2RS)-(4-bromo-phenyl)-[4-[2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy]-phenyl]-methanone.fumarate (1:1), m.p. 136-137° C.

Workup

  1. concentrationthe mixture is concentrated
  2. washwashed with saturated sodium bicarbonate solution and 10% sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in ether
  6. customprecipitated with hexane
  7. concentrationThe mother liquor is concentrated
  8. dissolutionthe crude (1RS,2RS)-(4-bromo-phenyl)-[4-[2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy]-phenyl]-methanone is dissolved in ethanol
  9. additiontreated with 2.7 g of fumaric acid
  10. customcrystallized out

Sources & evidence

ORD record
ord-8c3ad2ef7d22455bae9aa043f6d01599
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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