Triethylamine → (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

HRID 1526867Notes

Reaction equation

HRID 1526867 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl.O>[CH3:22][S:23]([O:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:3]1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 216370811,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Product 1

HCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonateYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(1S,3R)-3-hydroxycyclopentyl]carbamate (3.0 g, 14.91 mmol, 1.00 equiv) and triethylamine (3.0 g, 29.65 mmol, 1.99 equiv) in dichloromethane (50 mL) was added methanesulfonyl chloride (2.2 g, 19.21 mmol, 1.29 equiv) dropwise with stiffing at 0-5° C. After addition was completed, the reaction mixture was warmed to room temperature and stirred at room temperature for 2 h. The mixture was diluted with 50 mL of water and extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 2×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.8 g (91%) of tert-butyl N-[(1S,3R)-3-(methane sulfonyloxy)cyclopentyl]carbamate as a white solid.

Workup

  1. customwith stiffing at 0-5° C
  2. additionAfter addition
  3. extractionextracted with 2×50 mL of ethyl acetate
  4. washThe combined organic layers was washed with 2×30 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b288f60a1f1048dfa1fc8a89c05a4bd3
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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