反応 #89637

反応方程式

(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

benzaldehyde

sodium triacetoxyborohydride

sodium carbonate

→

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

収率 54.4%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 18 h
2. 2
   workup.STIRRINGthe mixture stirred for a few minutes
3. 3
   抽出extracted with ethyl acetate (30 mL
4. 4
   洗浄The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each)
5. 5
   乾燥dried (MgSO4)
6. 6
   濃縮concentrated
7. 7
   その他isolated

実験手順

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) (166 mg, 0.42 mmol) in anhydrous 1,2-dichloroethane (5 mL) was treated with anhydrous sodium sulfate (2 g) and benzaldehyde (69 mg, 0.65 mmol), stirred for 2.5 h, then treated with sodium triacetoxyborohydride (212 mg, 1.0 mmol) and glacial acetic acid (2 drops) and stirred for 18 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-1-benzyl-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid (70 mg, 44%) as a white semisolid. NMR (d6-DMSO) δ 7.62 (br s, 2 H), 7.44 (br s, 3 H), 4.30-4.60 (m, 2 H), 3.60-3.90 (m, 2 H), 3.35-3.50 (m, 2 H), 2.85 (m, 1 H), 2.50 (m, 1 H), 1.20-1.80 (m, 3 H), 0.60-0.80 (m, 2 H). MS (m+1): 307.3; MS (m−H2O+1): 289.2.

出典