3-(dimethylamino)-2,2-dimethylpropanal

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 22.14 g 3-aminopropyltriethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). Yield: 32.3 g of a clear, colorless oil having an amine content of 5.97 mmol N/g and a purity of 98%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 17.93 g 3-aminopropyltrimethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). The product was distilled after manufacture in order to remove oligomer portions. Yield: 28.4 g of a clear, colorless oil having an amine content of 6.61 mmol N/g and a purity of 95%. The product was distilled after manufacture in order to remove oligomer portions

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 3-dimethylamino-2,2-dimethylpropionaldehyde (91 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-(3-(dimethylamino)-2,2-dimethylpropyl)pyrrolidine-3-carboxylic acid (36 mg, 16%) as a white granular solid. NMR (D2O) δ 3.80-4.00 (m, 2 H), 3.35-3.50 (m, 3 H), 3.20 (s, 2 H), 2.89 (s, 6 H), 2.50-2.65 (m, 1 H), 1.50-1.65 (m, 1 H), 1.25-1.35 (m, 2 H), 1.21 (s, 6 H), 0.65-0.75 (m, 2 H). MS (m−H2O+1): 312.0; MS (m−2 H2O+1): 294.4. stirred for 16 h the mixture stirred for a few minutes extracted with ethyl acetate (30 mL The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each) dried (MgSO4) concentrated isolated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 3-dimethylamino-2,2-dimethylpropionaldehyde (91 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-(3-(dimethylamino)-2,2-dimethylpropyl)pyrrolidine-3-carboxylic acid (36 mg, 16%) as a white granular solid. NMR (D2O) δ 3.80-4.00 (m, 2 H), 3.35-3.50 (m, 3 H), 3.20 (s, 2 H), 2.89 (s, 6 H), 2.50-2.65 (m, 1 H), 1.50-1.65 (m, 1 H), 1.25-1.35 (m, 2 H), 1.21 (s, 6 H), 0.65-0.75 (m, 2 H). MS (m−H2O+1): 312.0; MS (m−2 H2O+1): 294.4. stirred for 16 h the mixture stirred for a few minutes extracted with ethyl acetate (30 mL The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each) dried (MgSO4) concentrated isolated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 22.14 g 3-aminopropyltriethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). Yield: 32.3 g of a clear, colorless oil having an amine content of 5.97 mmol N/g and a purity of 98%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 22.14 g 3-aminopropyltriethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). Yield: 32.3 g of a clear, colorless oil having an amine content of 5.97 mmol N/g and a purity of 98%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 17.93 g 3-aminopropyltrimethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). The product was distilled after manufacture in order to remove oligomer portions. Yield: 28.4 g of a clear, colorless oil having an amine content of 6.61 mmol N/g and a purity of 95%. The product was distilled after manufacture in order to remove oligomer portions

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 17.93 g 3-aminopropyltrimethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). The product was distilled after manufacture in order to remove oligomer portions. Yield: 28.4 g of a clear, colorless oil having an amine content of 6.61 mmol N/g and a purity of 95%. The product was distilled after manufacture in order to remove oligomer portions

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 3-dimethylamino-2,2-dimethylpropionaldehyde (91 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-(3-(dimethylamino)-2,2-dimethylpropyl)pyrrolidine-3-carboxylic acid (36 mg, 16%) as a white granular solid. NMR (D2O) δ 3.80-4.00 (m, 2 H), 3.35-3.50 (m, 3 H), 3.20 (s, 2 H), 2.89 (s, 6 H), 2.50-2.65 (m, 1 H), 1.50-1.65 (m, 1 H), 1.25-1.35 (m, 2 H), 1.21 (s, 6 H), 0.65-0.75 (m, 2 H). MS (m−H2O+1): 312.0; MS (m−2 H2O+1): 294.4. stirred for 16 h the mixture stirred for a few minutes extracted with ethyl acetate (30 mL The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each) dried (MgSO4) concentrated isolated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 3-dimethylamino-2,2-dimethylpropionaldehyde (91 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-(3-(dimethylamino)-2,2-dimethylpropyl)pyrrolidine-3-carboxylic acid (36 mg, 16%) as a white granular solid. NMR (D2O) δ 3.80-4.00 (m, 2 H), 3.35-3.50 (m, 3 H), 3.20 (s, 2 H), 2.89 (s, 6 H), 2.50-2.65 (m, 1 H), 1.50-1.65 (m, 1 H), 1.25-1.35 (m, 2 H), 1.21 (s, 6 H), 0.65-0.75 (m, 2 H). MS (m−H2O+1): 312.0; MS (m−2 H2O+1): 294.4. stirred for 16 h the mixture stirred for a few minutes extracted with ethyl acetate (30 mL The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each) dried (MgSO4) concentrated isolated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 3-dimethylamino-2,2-dimethylpropionaldehyde (91 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-(3-(dimethylamino)-2,2-dimethylpropyl)pyrrolidine-3-carboxylic acid (36 mg, 16%) as a white granular solid. NMR (D2O) δ 3.80-4.00 (m, 2 H), 3.35-3.50 (m, 3 H), 3.20 (s, 2 H), 2.89 (s, 6 H), 2.50-2.65 (m, 1 H), 1.50-1.65 (m, 1 H), 1.25-1.35 (m, 2 H), 1.21 (s, 6 H), 0.65-0.75 (m, 2 H). MS (m−H2O+1): 312.0; MS (m−2 H2O+1): 294.4. stirred for 16 h the mixture stirred for a few minutes extracted with ethyl acetate (30 mL The combined organic solution was washed with water and saturated aqueous sodium chloride (20 mL each) dried (MgSO4) concentrated isolated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.57 g 2,2-dimethyl-3-dimethylaminopropanal, 7.45 g 2-propanamine and 22.14 g 3-aminopropyltriethoxysilane were reacted according to the general manufacturing procedure (iminosilanes). Yield: 32.3 g of a clear, colorless oil having an amine content of 5.97 mmol N/g and a purity of 98%.