p-Toluenesulfonic acid monohydrate → HCID 86599621, compound

HRID 505442Notes

Reaction equation

HRID 505442 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]#[N:15])=O)(C)(C)C.O.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(#N)C>[OH:13][C@H:11]1[CH2:12][NH:8][C@H:9]([C:14]#[N:15])[CH2:10]1.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([O-:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 24903573(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine

Product 1

HCID 86599621HCID 86599621, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.40 g (30 mmol) of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-pyrrolidine-2-carbonitrile was dissolved in 100 ml of acetonitrile and 8.56 g (45 mmol) of 4-methylbenzenesulphonic acid monohydrate was added to the solution. The mixture was stirred at room temperature for 24 hours and was evaporated under reduced pressure. 500 ml of diethyl ether was added to the resulting brown oil. It was stirred 10 minutes and kept in the refrigerator for a night. The resulting white crystalline material was filtered off and washed with diethyl ether. 6.31 g (73%) of the above product are obtained. M.p.: 110-113° C.

Workup

  1. customwas evaporated under reduced pressure
  2. addition500 ml of diethyl ether was added to the resulting brown oil
  3. stirringIt was stirred 10 minutes
  4. waitkept in the refrigerator for a night
  5. filtrationThe resulting white crystalline material was filtered off
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2cda63b4719f4cb3886697187a10367a
Source dataset
uspto-grants-2010_08
Patent number
US07781455B2

Reaction notes

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