Pyridine → HCID 178505694, compound

HRID 397169Notes

Reaction equation

HRID 397169 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][C@H:10]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18]O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.FC1C=CC(C[C@H]2CC[C@H](N3CCC[C@H]3CO)CC2)=CC=1.N1C=CC=CC=1.C1(C)C=CC(S([Cl:58])(=O)=O)=CC=1>C(Cl)Cl.C(OCC)(=O)C>[Cl:58][CH2:18][C@@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C@H:10]1[CH2:11][CH2:12][C@@H:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 178520997HCID 178520997, compoundHCID 178520998HCID 178520998, compound

Product 1

HCID 178505694HCID 178505694, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of {(2S)-1-[cis-4-(4-fluorobenzyl)cyclohexyl]pyrrolidinyl}methanol and {(2S)-1-[trans-4-(4-fluorobenzyl)cyclohexyl]pyrrolidinyl}methanol (390 mg, 1.34 mmol) in 5 ml of methylene chloride at 25° C. under N2 was added pyridine (0.22 ml, 2.75 mmol, EM Science) followed by p-toluenesulfonyl chloride (288 mg, 1.51 mmol, Aldrich). Worked up after 16 hours by adding ethyl acetate then rinsing 3 times with sat'd sodium bicarbonate followed by 1 time time with brine. The organic was dried over magnesium sulfate, and concentrated in vacuo to obtain an oil which was purified over silica gel in 100% ethyl acetate to yield 87 mg of product. MS (ESI) detects 310 (M+H). The other isomer was isolated and used for example 16.

Workup

  1. washthen rinsing 3 times with sat'd sodium bicarbonate
  2. dry with materialThe organic was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain an oil which
  5. customwas purified over silica gel in 100% ethyl acetate

Sources & evidence

ORD record
ord-343edf923eb64aca9170fddb2416c92d
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

Loading…