Bromomethylcyclopropane → HCID 68681688, compound

HRID 2263617Notes

Reaction equation

HRID 2263617 reaction equation
[CH:1]1([CH2:4][S:5][CH:6]2[CH2:11][CH2:10][CH:9]([C:12]#[N:13])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>C1COCC1>[CH:14]1([CH2:17][C:9]2([C:12]#[N:13])[CH2:10][CH2:11][CH:6]([S:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:7][CH2:8]2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68682374HCID 68682374, compound

Product 1

HCID 68681688HCID 68681688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile (either isomer) (1.95 g; 10 mmol) was dissolved in THF (10 mL) and cyclopropyl methyl bromide (2.7 g; 20 mmol) was added followed by the dropwise addition of sodium hexamethyldisilazide (2M, 10 mL, 20 mmol). The reaction was stirred for half an hour and then was quenched with brine and extracted into ethyl acetate. The organic layer was dried and product was purified rigorously from its less polar isomer on silica using a Biotage 65i cartridge eluting with EtOAc/isohexane to yield 1-(cyclopropylmethyl)-4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile as an oil. (2 g, 80%)

Workup

  1. customwas quenched with brine
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was dried
  4. customproduct was purified rigorously from its less polar isomer on silica using a Biotage 65i cartridge
  5. washeluting with EtOAc/isohexane

Sources & evidence

ORD record
ord-0c14728d167747f88691b833fc8c6e37
Source dataset
uspto-grants-2010_12
Patent number
US07851638B2

Reaction notes

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