Sodium Iodide → tert-butyl N-[(1S,3S)-3-iodocyclopentyl]carbamate

HRID 931489Notes

Reaction equation

HRID 931489 reaction equation
CS(O[C@@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1)(=O)=O.[I-:19].[Na+]>CC(C)=O.O>[I:19][C@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

Product 1

HCID 86709136tert-butyl N-[(1S,3S)-3-iodocyclopentyl]carbamateYield 43%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl N-[(1S,3R)-3-(methanesulfonyloxy)cyclopentyl]carbamate (2.1 g, 7.52 mmol, 1.00 equiv) and sodium iodide (7 g, 46.70 mmol, 6.21 equiv) in acetone (40 mL) was stirred at 50° C. for 30 min. The reaction mixture was diluted with 100 mL of water then extracted with 2×30 mL of ethyl acetate. The combined organic layers was washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/5) to give 1.0 g (43%) of tert-butyl N-[(1S,3S)-3-iodocyclopentyl]carbamate as a white solid.

Workup

  1. extractionthen extracted with 2×30 mL of ethyl acetate
  2. washThe combined organic layers was washed with 2×50 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/5)

Sources & evidence

ORD record
ord-5c5f21638fec4bc48849866fcd16b6a1
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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