Tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate → Tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

HRID 1804579Notes

Reaction equation

HRID 1804579 reaction equation
[Si]([O:8][C@H:9]([C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[N:11]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C(C)(C)C)(C)C>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[OH:8][C@H:9]([C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:21]=2)[N:11]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]

Participants

4

Reactant 1

HCID 86666749Tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

Product 1

HCID 68396456Tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylateYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11078149TBAF tetrahydrofuranSolvent

Procedure

A solution of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (11.0 g, 20.3 mmol) in 100 mL of 2 M tetrabutylammonium fluoride tetrahydrofuran solution was stirred at RT overnight. The mixture was then diluted with water and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated to afford 8.51 g (98%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 2H), 7.93 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.0 Hz, 1H), 7.34-7.28 (m, 3H), 6.36 (s, 1H), 4.54 (d, J=8.5 Hz, 1H), 4.18-4.09 (m, 2H), 3.92 (s, 3H), 3.23 (s, 1H), 3.13-3.10 (m, 1H), 2.61-2.52 (m, 1H), 1.78-1.60 (m, 2H), 1.49 (s, 9H). MS: m/z (ESI) 427 (M+1).

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a83d3815b8d4c25b97adc4f3ac7d32c
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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