Water → 2-(Benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonate

HRID 451797Notes

Reaction equation

HRID 451797 reaction equation
[C:1]12([CH2:9][CH:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][OH:12])[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C(Cl)Cl>[CH3:24][S:25]([O:12][CH2:11][CH:10]([NH:13][C:14]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:23])[CH2:9][C:1]12[CH2:2][CH2:3][CH:4]([CH2:5][CH2:6]1)[CH2:7][CH2:8]2)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 59201578Benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate

Product 1

HCID 592014412-(Benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonateYield 132.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate (668 mg, 2.1 mmol, 1 eq.), TEA (638 mg, 6.3 mmol, 3 eq.) in CH2Cl2 (100 mL) was added dropwise MsCl (289 mg, 2.52 mmol, 1.2 eq.) at 0-5° C. The resulting mixture was stirred for 2 hrs. Then the mixture was poured into water (20 mL) and extracted with CH2Cl2 (20 mL×4). The organic phase was combined and evaporated to give 2-(benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonate (1.1 g, crude) as oil, which was used in the next step without further purification.

Workup

  1. extractionextracted with CH2Cl2 (20 mL×4)
  2. customevaporated

Sources & evidence

ORD record
ord-d8db4fa7b36a4ee8b5a4ad6934c5b02d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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