2,6-Lutidine → (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

HRID 2208145Notes

Reaction equation

HRID 2208145 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8]1.N1C(C)=CC=CC=1C>ClCCl>[CH3:1][S:2]([O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 216370811,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methansulfonyl chloride (8.2 g; 72.0 mmol) is slowly added to an ice cold solution of commercially available tert-butyl [(1S,3R)-3-hydroxycyclopentyl]carbamate (12.1 g; 60.0 mmol) and 2,6-lutidine (9.6 g; 90.0 mmol) in dry dichloromethane (300 mL). The stirred reaction mixture is allowed to warm to ambient temperature over night. The reaction mixture is extracted with water, ice cold 1N HCl, half saturated brine, and dried over MgSO4. After filtration through a pad of neural alumina (act. 2-3) the solvent is removed under reduced pressure to yield the crude title compound as yellow oil that is processed without additional purification.

Workup

  1. customThe stirred reaction mixture
  2. extractionThe reaction mixture is extracted with water, ice cold 1N HCl, half saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration through a pad of neural alumina (act. 2-3) the solvent
  5. customis removed under reduced pressure

Sources & evidence

ORD record
ord-a47af30337f84878b0d72839db91bfa9
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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