Triethylamine → 3-Methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

HRID 897257Notes

Reaction equation

HRID 897257 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([OH:14])[CH2:10]2)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 583468323-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

Product 1

HCID 583468803-Methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (1.250 g, 6.28 mmol) in dichloromethane (62 mL) was added triethylamine (1.40 mL, 10.0 mmol) and methanesulfonyl chloride (0.722 mL, 9.38 mmol) dropwise. The solution was stirred 2 hrs, washed with sodium bicarbonate, dried over MgSO4, filtered, and concentrated. The crude oil (1.74 g) was taken on with no purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.26 (t, J=7.1 Hz, 3H), 2.04 (m, 6H), 2.18 (m, 2H), 3.02 (s, 3H), 4.14 (q, J=7.1 Hz, 2H), 4.29 (m, 2H), 5.02 (m, 1H); MS (ESI+Q1MS) m/z 278 [M+H]+

Workup

  1. washwashed with sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude oil (1.74 g) was taken on with no purification

Sources & evidence

ORD record
ord-c1f6aa7c3bcf4cf8b32230a82d57a209
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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