Tert-Butylamine → Boc-Hyp-NH-tBu

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Reaction Steps

The N-protected acid (17.5 g, 75.6 mmol, described in section (a) of example 1) was dissolved in CH2Cl2 (300 mL) and DIEA (13 mL, 76.6 mmol). tert-Butylamine (8.73 mL, 83.1 mmol ) was added to the solution, followed by the addition of BOP (40 g, 90.7 mmol) and DIEA (13 mL, 151 mmol). The mixture was stirred at room temperature for 7 h and then diluted with EtOAc. The organic phase was separated, washed with a saturated aqueous solution of NaHCO3 (2×), H2O (2×) and brine (2×), dried (MgSO4) and evaporated to dryness. The solid residue was triturated with Et2O/EtOAc (9:1), collected on a filter, washed with Et2O and dried to provide N-tert-butyl-1-(tert-butyloxycarbonyl)-4(R)-hydroxypyrrolidine-2(S)-carboxamide (15.6 g, 72%).

Provenance & Evidence