Diethyl Ether → 1,1-Dimethylethyl N-((1S,2S)-2-((methylsulfonyl)oxy)cyclohexyl)carbamate

HRID 546415Notes

Reaction equation

HRID 546415 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(OCC)C>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[O:15][S:17]([CH3:16])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 10013520(1S,2S)-trans-N-Boc-2-Aminocyclohexanol

Product 1

HCID 588220891,1-Dimethylethyl N-((1S,2S)-2-((methylsulfonyl)oxy)cyclohexyl)carbamateYield 71.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(1S,2S)-2-tert-Butoxycarbonylamino-1-cyclohexanol (646 mg) was dissolved in pyridine (4 ml), methane-sulfonyl chloride (378 mg) was added with ice cooling, and the mixture was stirred for 5 hours. After diethyl ether was added to the reaction mixture and washed 5 times with water, the resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (630 mg) as colorless crystals.

Workup

  1. washwashed 5 times with water
  2. dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-090810a7a63a460c91a036cb167b915a
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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