Sodium Chloride → tert-Butyl ((3S,4S)-4-aminotetrahydrofuran-3-yl)carbamate

HRID 397165Notes

Reaction equation

[O:1]1[CH2:5][C@@H:4]([NH2:6])[C@H:3]([NH2:7])[CH2:2]1.C([Li])CCC.[C:13](OC([O-])=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Cl-].[Na+]>O1CCCC1>[C:16]([O:15][C:13](=[O:14])[NH:6][C@@H:4]1[CH2:5][O:1][CH2:2][C@H:3]1[NH2:7])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

A flame-dried round bottom flask under nitrogen was charged with dry tetrahydrofuran (17 mL) and ((3S,4S)-tetrahydro-3,4-furandiamine (170 mg, 1.70 mmol) prepared according to the procedures of Skarzewski, J., et al. Tetrahedron: Asymmetry 1997, 8 (11), 1861. The solution was cooled to −78° C., and 2.5 M n-butyl lithium in hexanes (700 μL, 1.75 mmol) was added. The resulting cloudy white suspension was warmed to 23° C., and the suspension became orange. After 10 min, tert-butyl dicarbonate (371 mg, 1.70 mmol) was added in one portion. An additional 100 mg-portion of tert-butyl dicarbonate was added after 10 min. The reaction was then poured into saturated aqueous sodium chloride (50 mL), and the aqueous layer was washed with ethyl acetate (4×20 mL). The combined organic layers were dried over sodium sulfate, concentrated, and the resulting residue was purified by flash chromatography (5-10% methanol in dichloromethane) to yield the desired amine (90 mg, 26%) as a yellow oil. MS (ESI) 203 (M+H).

Workup

temperatureThe resulting cloudy white suspension was warmed to 23° C.
washthe aqueous layer was washed with ethyl acetate (4×20 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated
customthe resulting residue was purified by flash chromatography (5-10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-63d1fc92191c4da5ba5cf2ad449dc37d
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608227B1

Reaction notes

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