Water → tert-Butyl [(1S,2S)-2-hydroxycyclopentyl]carbamate

HRID 245054Notes

Reaction equation

HRID 245054 reaction equation
C[Si](C)(C)[O:3][C@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:3][C@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86693768HCID 86693768, compound

Product 1

HCID 10104271tert-Butyl [(1S,2S)-2-hydroxycyclopentyl]carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl N-[(1S,2S)-2-trimethylsilyloxycyclopentyl]carbamate (15.5 g, 56.7 mmol) and tetrabutylammonium fluoride (85.0 mL, 85.0 mmol) in THF (113 mL) are stirred at room temperature for 1 h. Water (50 mL) is added and the mixture is concentrated in vacuo to remove the THF. The resulting mixture is extracted with EtOAc (3×75 mL). The combined organic portions are washed with brine (2×30 mL), dried over sodium sulfate, filtered, and concentrated to give 14.7 g of crude product as a yellow oil. The material is purified on silica gel (330 g) using 25% EtOAc/hexanes to give the title compound as a white solid (10.25 g, 90%). LC-ES/MS m/z 224 (M+Na).

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. customto remove the THF
  3. extractionThe resulting mixture is extracted with EtOAc (3×75 mL)
  4. washThe combined organic portions are washed with brine (2×30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 14.7 g of crude product as a yellow oil
  9. customThe material is purified on silica gel (330 g)

Sources & evidence

ORD record
ord-99f9601105c54380970defca2c26fa8b
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

Loading…