Bromocyclopropane → HCID 86660375, compound

HRID 2167364Notes

Reaction equation

HRID 2167364 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15](=O)[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1(Br)C[CH2:19]1.O[Li].O>C(O)(C)C.O>[CH:16]1([CH2:15][S:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 78037BromocyclopropaneHCID 168937Lithium hydroxide, monohydrateHCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

Product 1

HCID 86660375HCID 86660375, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

To an argon purged solution of tert-butyl-4-(acetylthio)piperidine-1-carboxylate (51, 1.50 g, 5.86 mmol) in a 5:1 mixture of isopropanol-water (55 mL) was added cyclopropyl bromide (1.52 g, 11.72 mmol) followed by solid LiOH.H2O (1.0 g, 68.67 mmol). The mixture stirred at room temperature and stirred for 16 h and was concentrated under reduced pressure. The residue was dissolved in EtOAc (90 mL) and washed with H2O (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give tert-butyl 4-(cyclopropylmethylthio)piperidine-1-carboxylate as a colorless syrup (52, 1.1 g, 69%); 1H NMR (300 MHz, CDCl3) δ 2.98-2.75 (m, 3H), 2.61 (m, 1H), 2.48 (d, J=6.9 Hz, 2H), 2.39-2.28 (m, 1H), 1.74-2.01 (m, 2H), 1.43-1.55 (m, 2H), 1.45 (s, 9H), 1.01-0.88 (m, 1H), 0.52-0.59 (m, 2H), 0.15-0.25 (m, 2H);

Workup

  1. stirringstirred for 16 h
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (90 mL)
  4. washwashed with H2O (25 mL), brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36dd3653b4564caeaf2583089f72c795
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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