Tetrabutylammonium Fluoride → trans-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine

HRID 350516Notes

Reaction equation

HRID 350516 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([N:13]([CH3:15])[CH3:14])[CH2:10][C@H:9]1[CH2:16][O:17][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([N:13]([CH3:14])[CH3:15])[CH2:10][C@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69334202trans-1-tert-butoxycarbonyl(2S)-(tert-butyldiphenylsilyloxy)methyl-4-dimethylaminopyrrolidine

Product 1

HCID 20737863trans-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidineYield 108.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trans-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy)methyl-4-dimethylaminopyrrolidine (330 mg, 0.68 mmol) in THF (5 ml) was added TBAF (1.0 M solution in THF, 1.0 ml, 1.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (3:97 to 20:80, v/v) as eluent to give trans-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine (180 mg, quant.) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.47 (s, 9H), 2.23 (s, 6H), 1.65–1.75 (m, 2H), 2.75–4.10 (m, 4H), 3.61 (d, J=5.6 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (3:97 to 20:80

Sources & evidence

ORD record
ord-bb44cc7a1d9d43d9b4fb4c077b1485b8
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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