Acetone → Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

HRID 1386772Notes

Reaction equation

HRID 1386772 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[I-:19].[Na+].[CH3:21]C(C)=O>>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:21][I:19])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

Procedure

A mixture of 1-(t-butoxycarbonyl)piperidin-4-yl methanesulfonate (13.58 g, 46.4 mmol) and sodium iodide (34.68 g, 232 mmol) in acetone (80 mL) was heated to reflux for 3 h. The mixture was partitioned between ether (350 mL) and H2O (350 mL). The organic layer was washed with saturated aq. NaCl (250 mL), and the aqueous layers were extracted in succession with ether (250 mL). The combined organic layers were dried (Na2SO4), decanted, and evaporated to give 14.8 g of 1-(t-butoxycarbonyl)-4-(iodomethyl)piperidine as a pale yellow oil. 1H NMR (500 MHz) δ 4.25-4.00 (m, 2H), 3.12 (d, J=4, 2H), 2.78-2.52 (m, 2H), 1.85 (d, J=13, 2H), 1.68-1.56 (m, 1H), 1.48 (s, 9H), 1.15 (qd, J=12, 4, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe mixture was partitioned between ether (350 mL) and H2O (350 mL)
  4. washThe organic layer was washed with saturated aq. NaCl (250 mL)
  5. extractionthe aqueous layers were extracted in succession with ether (250 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customdecanted
  8. customevaporated

Sources & evidence

ORD record
ord-8c07d98c9a234496828ac66679a7164d
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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