(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

INTERMEDIATE 12(35INTERMEDIATE 13(3.S'.4.Sr)-3-(fert-ButoxycarbonylaminoV4-hydroxypyrrolidine-l -carboxylic acid tert-buty esterTo a solution of Intermediate 12 (700 mg, 5.0 mmol) in 1, 4-dioxane (30 mL) was added sodium hydroxide (300 mg, 7.5 mmol) and di-tert-butyl dicarbonate (1.6 g, 7.5 mmol) and the mixture stirred for 18 h. After this time the reaction mixture was diluted with ethyl acetate (30 mL) and washed with water (25 mL), dried (Na2SO4) and evaporated in vacuo to give the title compound as a colourless oil (1.4 g, 93%). 5H (DMSO-d6) 7.02 (IH, s), 5.18 (IH, m), 3.96 (IH, m), 3.57 (IH, m), 3.42 (2H, m), 3.08 (2H, m), 1.40 (18H, s).A mixture of 6-chloro-2, 2-dimethyl-5-nitro-2, 3-dihydrobenzofuran (Intermediate A) (200mg, 0.88 mmol) and A solution of tert-butyl (3S, 4S)-3-amino-4-hydroxypyrrolidine-l-carboxylate (355.5 mg, 1.758 mmol) in DCM (2 mL) was treated with DIEA (921.0 jiL, 5.273 mmol) then stirred for 30 min at 0 C. The 0 C mixture was treated dropwise with isovaleryl chloride (235.7 mu^, 1.933 mmol). The resulting mixture was stirred for 20 min, over which time the temperature was allowed to gradually reach ambient temperature. The reaction mixture was diluted with DCM, and washed with saturated NaHC03(aq). The organic extracts were directly purified by silica chromatography (using 20-100% EtOAc in Hexanes as the gradient eluent) to cleanly provide the title compound (487.2 mg, 97% yield). MS (apci) m/z = 187.2 ([M - boc]+H).

(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine is used as a pharmaceutical intermediate.

Molecular Weight:202.25
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:202.13174244
Monoisotopic Mass:202.13174244
Topological Polar Surface Area:75.8
Heavy Atom Count:14
Complexity:225
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes