1-Boc-3-hydroxymethylpyrrolidine

900 g of pyrrolidine-3-methanol was dissolved in 4.5 L of dichloromethane, 900 g of di-tert-butyl dicarbonate and 1.8 kg of triethylamine were added in portions, Room temperature reaction for about 5 hours, Add water quenching reaction, The N-Boc-pyrrolidine-3-methanol was treated in a conventional manner, Yield 95percent.To a solution of pyrrolidin-3-ylmethanol (597mg, 5.90 mmol) in THF (12 mL, 0.5M) was added di-tert-butyl dicarbonate (1.352 g, 6.20 mmol) and the mixturewas stirred for 14 h and subsequently concentrated in vacuo to provide the crude product that was purified bysilica gel chromatography to provide S1d (610 mg, 3.03 mmol, 51percent yield)A suspension of LiAlHTo an ice cooled solution of 1-Boc-pyrrolidine-3-carboxylic acid (1 g, 4.64 mmol) in dry tetrahydrofuran (6 ml) Borane-methyl sulfide complex (2M in tetrahydrofuran) (3.48 ml, 6.96 mmol) was added dropwise the under NTo a solution of pyrrolidine-1, 3-dicarboxylic acid1-tert-butyl ester 3-ethyl ester (10.4 g, 42.9 mmol) in tetrahydrofuran(50 mL) and methanol (50mL) at 0 C was added sodium borohydride (NaBH4) (3.25 g, 86 mmol) in portions over 30 minutes. After 18 hours, more NaBH4 (3.25 g, 86 mmol) was added. After a further 24 hours, the reaction mixture was diluted with ethyl acetate, quenched with saturated aqueousNa2C03 and stirred for 15 minutes. The layers were separated, the aqueous layer extracted with ethyl acetate, and then the combined organic layers washed twice with water, once with brine, dried(Na2SO4) and concentrated under reduced pressure. The crude product was purified by column To a solution of pyrrolidine-1, 3-dicarboxylic acid1-tert-butyl ester 3-ethyl ester (10.4 g, 42.9 mmol) in tetrahydrofuran (50 mL) and methanol (50mL) at 0 C was added sodium borohydride(NaBH4) (3.25 g, 86 mmol) in portions over 30 minutes. After 18 hours, more NaBH4 (3.25 g, 86 mmol) was added. After a further 24 hours, the reaction mixture was diluted with ethyl acetate, quenched with saturated aqueousNa2CO3 and stirred for 15 minutes. The layers were separated, the aqueous layer extracted with ethyl acetate, and then the combined organic layers washed twice with water, once with brine, dried(Na2S04) and concentrated under reduced pressure. The crude product was purified by column 3-Formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3 g, 15.0 mmol) was taken in methanol (50 mL) and sodium borohydride (0.8 g, 22.5 mmol) was added in portions at room temperature and stirred for 1 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (pet ether/ethyl acetate 20percent) to provide the titled compound (66percent, 2 g, colorless liquid). The synthesis started with preparing amine 2-5. To a solution of scheme 34 compound 2-1 ( 4 g, 0.02 mol) in THF/MeOH (16 mL/16 mL) at 0 °C was added NaBH

Molecular Weight:201.26
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:201.13649347
Monoisotopic Mass:201.13649347
Topological Polar Surface Area:49.8
Heavy Atom Count:14
Complexity:210
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes