TBAF tetrahydrofuran → HCID 59383028, compound

HRID 451779Notes

Reaction equation

HRID 451779 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C1COCC1>O>[CH:12]1([CH2:11][C@H:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:9][OH:8])[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 58246966tert-Butyl (S)-3-cyclopentyl-1-(t-butyldimethylsilyloxy)propan-2-ylcarbamate

Product 1

HCID 59383028HCID 59383028, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopentylpropan-2-ylcarbamate (2.9 g, 8.1 mmol) was treated with 1 M Bu4NF/THF (24.3 mL) at 0° C. for 1 h. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×40 mL). The organic layers were washed with saturated aqueous brine, dried over MgSO4, and evaporated to give crude (S)-tert-butyl 1-cyclopentyl-3-hydroxypropan-2-ylcarbamate that was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 4.60 (brs, 1H), 3.68 (m, 2H), 3.52 (m, 1H), 1.81 (m, 3H), 1.60 (m, 3H), 1.50 (m, 3H), 1.44 (s, 9H), 1.09 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×40 mL)
  2. washThe organic layers were washed with saturated aqueous brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-8f47a2151dcf4a778a42c6b425e20faf
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…