Hexylamine → HCID 86599750, compound

HRID 1393917Notes

Reaction equation

HRID 1393917 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]1=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:19](Cl)(Cl)(Cl)=[O:20].[CH2:24]([NH2:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([P:19]([NH:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([NH:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:20])[C:13]1=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8102HexylamineHCID 24813Phosphorus oxychlorideHCID 11482034Benzyl [(3S)-2-oxopiperidin-3-yl]carbamate

Product 1

HCID 86599750HCID 86599750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3S)-3-benzyloxycarbonylamino-2-piperidone (2.48 g, 9.99 mmol) in tetrahydrofuran (25 mL) was cooled at an external temperature of −78° C., followed by adding dropwise thereto an n-butyllithium-hexane solution (1.54 M, 6.2 mL, 9.548 mmol) over a period of 10 minutes, and the resulting mixture was stirred at the same temperature for 1.5 hours. Subsequently, a solution of phosphorus oxychloride (1.53 g, 9.98 mmol) in tetrahydrofuran (5 mL) was added thereto and stirred for 1.25 hours, after which n-hexylamine (d=0.76, 6.0 mL, 45.06 mmol) was added thereto and the resulting mixture was stirred at room temperature for 10 minutes.

Workup

  1. additionby adding dropwise
  2. stirringstirred for 1.25 hours
  3. stirringthe resulting mixture was stirred at room temperature for 10 minutes

Sources & evidence

ORD record
ord-db3f9d202367461b8ec6121a666081fd
Source dataset
uspto-grants-2008_03
Patent number
US07348318B2

Reaction notes

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