تفاعل #89643
ord-52a85f3115cc40fcbd1334475b362c5d
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1workup.STIRRINGstirred for 16 h
- 2workup.STIRRINGthe mixture stirred for a few minutes
- 3استخلاصextracted with ethyl acetate (30 mL
- 4غسيلThe combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each)
- 5تجفيفdried (MgSO4)
- 6تركيزconcentrated
- 7أخرىisolated
الإجراء التجريبي
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) (198 mg, 0.5 mmol) in anhydrous 1,2-dichloroethane (5 mL) was treated with anhydrous sodium sulfate (1 g) and quinoline-4-carboxaldehyde (110 mg, 0.7 mmol), stirred for 2 h, then treated with sodium triacetoxyborohydride (212 mg, 1.0 mmol) and glacial acetic acid (2 drops) and stirred for 16 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-(quinolin-4-ylmethyl)pyrrolidine-3-carboxylic acid (49 mg, 23%) as a pale amber solid. NMR (D2O) δ 9.12 (d, J=5.5 Hz, 1 H), 8.41 (d, J=8.5 Hz, 1 H), 8.23 (d, J=8.5 Hz, 1 H), 8.10-8.20 (m, 2 H), 8.00 (t, J=8.5 Hz, 1 H), 5.30 (m, 2 H), 4.06 (d, J=12.5 Hz, 1 H), 3.83 (m, 2 H), 3.51 (t, J=11.5 Hz, 1 H), 2.50-2.70 (m, 1 H), 1.60 (m, 1 H), 1.15-1.30 (m, 3 H), 0.60-0.70 (m, 2 H). MS (m−H2O+1): 340.3; MS (m−2H2O+1): 322.1.