Triphenylphosphine → HCID 68523985, compound

HRID 1470243Notes

Reaction equation

HRID 1470243 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10]O)[CH2:4][CH2:3]1.[C:12]([NH:19][C:20](=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[S:21][CH3:22])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:8][CH2:9][CH2:10][N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20](=[N:19][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[S:21][CH3:22])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 5462977Diethyl azodicarboxylateHCID 155406773-(1-Methylpiperidin-4-yl)propan-1-ol

Product 1

HCID 68523985HCID 68523985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2 °C

Procedure

To a 25 mL round bottom flask were added 3-(1-methyl-piperidin-4-yl)-propan-1-ol (0.23 g, 0.0014 mol), 1,3-di-Boc-2-methylisothiourea (0.42 g, 0.0014 mol), PPh3 (0.42 g, 0.0016 mol) and THF (anhydrous, 8.0 mL). The resultant, stirred stirring solution was cooled to 2.0° C. To the resultant solution was then added DEAD (0.27 mL, 0.0016 mol) drop wise. The reaction was aged cold for 30 min, warmed to room temperature and aged for 14 h. The THF was removed via rotovap and the residue taken up in MTBE (10 mL). The resultant solution was extracted with saturated aqueous NaHCO3 (2×10 mL) and diluted with hexanes (20 mL). After 10 min, the resultant slurry was filtered and the filtrate concentrated via rotovap. The residue was taken up in hexanes (25 mL) and filtered after 10 min. The filtrate was concentrated to yield N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N′-di-Boc-methylisothiourea.

Workup

  1. stirringstirring solution
  2. temperaturewarmed to room temperature and aged for 14 h
  3. customThe THF was removed via rotovap
  4. extractionThe resultant solution was extracted with saturated aqueous NaHCO3 (2×10 mL)
  5. additiondiluted with hexanes (20 mL)
  6. waitAfter 10 min
  7. filtrationthe resultant slurry was filtered
  8. concentrationthe filtrate concentrated via rotovap
  9. filtrationfiltered after 10 min
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4ecd124024094586a563427d968da2d3
Source dataset
uspto-grants-2015_04
Patent number
US09006432B2

Reaction notes

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