Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (S)-tert-butyl 1-hydroxy-4-(1-methoxycyclopentyl)butan-2-ylcarbamate

HRID 451859Notes

Reaction equation

HRID 451859 reaction equation
[CH3:1][O:2][C:3]1([CH2:8][CH2:9][C@H:10]2[CH2:14][O:13]C(C)(C)[N:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7][CH2:6][CH2:5][CH2:4]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[OH:13][CH2:14][C@@H:10]([NH:11][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:9][CH2:8][C:3]1([O:2][CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59201438(S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201337(S)-tert-butyl 1-hydroxy-4-(1-methoxycyclopentyl)butan-2-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above (S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate (1170 mg, 3.5 mmol, 1.0 equiv) was dissolved in 40 mL of methanol. Camphorsulphonic acid (417 mg, 1.8 mmol, 0.5 equiv) was added and the mixture stirred for 4 h at ambient temperature. The mixture was quenched by addition of ca. 1 mL of NEt3 and the reaction evaporated. The residue was taken up in EtOAc, washed with brine, then dried over MgSO4, filtered through a pad of silica gel, and evaporated. This afforded 1.03 g (3.5 mmol, 100% yield) of the desired (S)-tert-butyl 1-hydroxy-4-(1-methoxycyclopentyl)butan-2-ylcarbamate.

Workup

  1. customThe mixture was quenched by addition of ca. 1 mL of NEt3
  2. customthe reaction evaporated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of silica gel
  6. customevaporated

Sources & evidence

ORD record
ord-b9e4f6dc78734842af14ccc0404ac97e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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