(Dimethyl sulfide)trihydroboron → HCID 13279956, compound

HRID 1249181Notes

Reaction equation

HRID 1249181 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH:20][C:21](=O)[CH2:22][O:23][CH3:24])[CH2:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].B.CSC>O1CCCC1>[CH3:24][O:23][CH2:22][CH2:21][NH:20][CH:13]([C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11][CH2:12]1)[CH2:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 13279955HCID 13279955, compound

Product 1

HCID 13279956HCID 13279956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (2 ml) was added dropwise to a solution of the methoxyacetamide (5 g) prepared as described above in dry tetrahydrofuran (20 ml) at 0°-5° C. This mixture was left at ambient temperature for 7 days, then poured onto ice-water basified and extracted into ether, washed with water, dried and evaporated to dryness to give an oil. This oil was treated as above with more borane-methyl sulphide to give N-(2-methoxyethyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]-3-ethyl pentylamine (b.p. 189°-190° C./1.5 mm Hg) as an oil.

Workup

  1. customprepared
  2. additionpoured onto ice-water
  3. extractionextracted into ether
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness
  7. customto give an oil

Sources & evidence

ORD record
ord-57b39d98fc13417f99db6225b6474702
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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