Methanol → HCID 59347897, compound

HRID 20819Notes

Reaction equation

HRID 20819 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:14]1([Li])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO.[BH4-].[Na+]>C1COCC1>[NH3:3].[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1([CH:12]([NH2:13])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59347775HCID 59347775, compoundHCID 178506676HCID 178506676, compound

Product 2

HCID 222AmmoniaHCID 59347897HCID 59347897, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-1-(2-methyl-1-pyrrolidinyl)cyclopentanecarbonitrile D39 (0.997 g; 5.6 mmol) in dry THF was cooled to −70° C. To this phenyllithium (1.7M in C6H14/ether, 1.1 equiv) was added slowly. The whole mixture was allowed to warm slowly to room temperature over 3 h with stirring under argon. Reaction cooled to 0° C. and methanol added followed by sodium borohydride (portionwise) and allowed to react at 20° C. overnight. The reaction was cooled to 0° C. and quenched with saturated sodium bicarbonate, extracted with ethyl acetate, dried (Na2SO4) and evaporated. The product was purified by chromatography on a 5 g SCX column eluting from 0-100% ethyl acetate in pet. ether, 0-10% methanol in ethyl acetate then 2% 0.880 ammonia in ethyl acetate to give the title compound as an oil (0.67 g; 46%) was obtained. Mass Spectrum (Electrospray LC/MS): Found 259 (MH+). C17H26N2 requires 258. Ret. time 1.19 min.

Workup

  1. customReaction
  2. temperaturecooled to 0° C.
  3. customto react at 20° C. overnight
  4. temperatureThe reaction was cooled to 0° C.
  5. customquenched with saturated sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe product was purified by chromatography on a 5 g SCX column
  10. washeluting from 0-100% ethyl acetate in pet. ether, 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-05764b65d0e3468fa9a7b1bb9d440218
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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