Triethylamine → rac-tert-butyl N-[(1R,3S)-3-[(methanesulfonyloxy)methyl]cyclopentyl]carbamate

HRID 245915Notes

Reaction equation

HRID 245915 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([NH:7][C@@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][O:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11962829Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

Product 1

HCID 18453418rac-tert-butyl N-[(1R,3S)-3-[(methanesulfonyloxy)methyl]cyclopentyl]carbamateYield 120.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, (cis-3-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester (500 mg, 2.21 mmol) was dissolved in dichloromethane (5 ml). The solution was cooled to 0° C. and triethylamine (0.40 ml, 2.87 mmol) was added followed by methanesulfonyl chloride (0.20 ml, 2.57 mmol). The reaction mixture was stirred at 0° C. for 45 min then quenched with water and extracted with dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give 780 mg of methanesulfonic acid (cis)-3-tert-butoxycarbonylamino-cyclopentylmethyl ester as a pale yellow oil which was used without further purification.

Workup

  1. customthen quenched with water
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9857102cdc7744d29a754121a02af8c2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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