Reaktion #89638

Reaktionsgleichung

(3R,4S)-3-acetamido-N-tert-butyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)pyrrolidine-3-carboxamide

sodium sulfate

pyridine-3-carboxaldehyde

sodium triacetoxyborohydride

sodium carbonate

→

(3R,4S)-3-amino-4-(3-boronopropyl)-1-(pyridin-3-ylmethyl)pyrrolidine-3-carboxylic acid

Ausbeute 84.5%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 20 h
2. 2
   workup.STIRRINGthe mixture stirred for a few minutes
3. 3
   Extraktionextracted with ethyl acetate (30 mL
4. 4
   WaschenThe combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each)
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated
7. 7
   Sonstigeisolated

Vorschrift

A stirred solution of (3R,4S)-3-acetamido-N-tert-butyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)pyrrolidine-3-carboxamide (Example 8, step 4) (175 mg, 0.443 mmol) in anhydrous 1,2-dichloroethane (5 mL) was treated with anhydrous sodium sulfate (1 g) and pyridine-3-carboxaldehyde (75 mg, 0.70 mmol), stirred for 2 h, then treated with sodium triacetoxyborohydride (212 mg, 1.0 mmol) and glacial acetic acid (2 drops) and stirred for 20 h. Aqueous sodium carbonate (10%, 5 mL) was added and the mixture stirred for a few minutes and extracted with ethyl acetate (30 mL, then 2×10 mL). The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each), dried (MgSO4), and concentrated. The crude material was deprotected and isolated using the method described for example 8, step 5 to afford (3R,4S)-3-amino-4-(3-boronopropyl)-1-(pyridin-3-ylmethyl)pyrrolidine-3-carboxylic acid (115 mg, 68%) as a white semisolid. NMR (d6-DMSO) δ 8.90 (m, 1 H), 8.74 (m, 1 H), 8.00 (m, 1 H), 7.12 (m, 1 H), 4.55-4.85 (m, 2 H), 3.10-4.00 (m, 3 H), 2.70-3.00 (m, 1 H), 1.70 (m, 2 H), 0.90-1.50 (m, 3 H), 0.55-0.70 (m, 2 H). MS (m+1): 308.4; MS (m−H2O+1): 290.4.

Quelle