Ammonia → Benzyl (3R)-piperidin-3-ylcarbamate

HRID 7288Notes

Reaction equation

HRID 7288 reaction equation
[NH3:1].CS(O[CH2:7][C@H:8]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:9][CH2:10][CH2:11]OS(C)(=O)=O)(=O)=O>C1COCC1>[NH:1]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:17][C:18](=[O:19])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66524788(R)-2-(((Benzyloxy)carbonyl)amino)pentane-1,5-diyl dimethanesulfonate

Product 1

HCID 1514176Benzyl (3R)-piperidin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Liquid ammonia (ca. 30 ml) was added to a solution of (2R)-2-{[(benzyloxy)carbonyl]amino}-5-[(methylsulfonyl)oxy]pentyl methanesulfonate (1 g) in THF (15 ml) at −78° C. in a bomb reaction vessel and then the resultant mixture was allowed to reach room temperature. After 46 h, the solution was concentrated under reduced pressure to give an off-white solid which was purified using SPE (silica, eluting with methanol, methanol:aqueous ammonia 95:5, 9:1) to give the title compound (0.587 g) as an off white solid.

Workup

  1. customto reach room temperature
  2. concentrationthe solution was concentrated under reduced pressure
  3. customto give an off-white solid which
  4. customwas purified
  5. washSPE (silica, eluting with methanol, methanol:aqueous ammonia 95:5, 9:1)

Sources & evidence

ORD record
ord-d7f656c0db30491b9bd260da1a6f071a
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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