Sodium borohydride → HCID 68682724, compound

HRID 1865475Notes

Reaction equation

HRID 1865475 reaction equation
[CH:1]1([CH2:4][C:5]2([C:16]#[N:17])[CH2:10][CH2:9][CH:8]([S:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[CH3:18][Mg]Br.C1(C)C=CC=CC=1.CCCCCC.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH:1]1([CH2:4][C:5]2([CH:16]([NH2:17])[CH3:18])[CH2:6][CH2:7][CH:8]([S:11][CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:9][CH2:10]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 21889329Toluene hexaneHCID 68681688HCID 68681688, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68682724HCID 68682724, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1-(cyclopropylmethyl)4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile (2 g; 8.0321 mmol) was dissolved in toluene (30 mL) and methylmagnesium bromide (8.6 ml; 12mL of a 1.4M solution in 3:1 toluene/hexane) was added and the reaction mixture was heated to reflux for 16 hours. The reaction was cooled to 0C. and methanol (12 mL) was added and the mixture was stirred for 15 minutes before adding sodium borohydride (0.315 g; 8.514026 mmol) and stirring for 0.5 hours at room temperature. The reaction was carefully quenched with 1 M hydrochloric acid (24 mL) and then extracted into ethyl acetate and purified using a 40M Biotage cartridge using 5% (2M ammonia in methanol)/DCM to yield (1-{1-(cyclopropylmethyl)-4-[(cyclopropylmethyl)thio]cyclohexyl}ethyl)amine. (1.6 g, 75%)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. stirringstirring for 0.5 hours at room temperature
  4. customThe reaction was carefully quenched with 1 M hydrochloric acid (24 mL)
  5. extractionextracted into ethyl acetate
  6. custompurified

Sources & evidence

ORD record
ord-d8f96ec8c451492085db4d6c9a3d9b62
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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