Acetic Acid → 4-(1,4-Dioxaspiro[4.5]decan-8-yl)morpholine

HRID 1924472Notes

Reaction equation

C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]1[C:19]2([CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CC(O)=O>ClCCCl>[O:15]1[C:19]2([CH2:24][CH2:23][CH:22]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 12 °C

Procedure

Sodium triacetoxyborohydride (382 g, 1.8 mol) was added in one portion to a mixture of 1,4-dioxaspiro[4.5]decan-8-one (200.0 g, 1.28 mol), morpholine (111.4 g, 1.28 mol) and glacial AcOH (73.2 mL, 1.28 mol) in 1,2-dichloroethane (4 L). A slightly exothermic reaction occurred accompanied by increase in temperature by 12° C. Then the mixture was stirred at room temperature overnight. The reaction was quenched by the addition of 10% aqueous NaOH (1.8 L) over a period of 20 min. The organic layer was separated, washed with brine (1 L), dried over MgSO4 and concentrated to afford 7 (237.66 g) as white solid. The aqueous layer was extracted with EtOAc (4×300 mL). Combined extracts were washed with brine (1 L), dried over MgSO4 and concentrated to furnish additional portion of 7 (44 g) as an off-white solid. Total yield of 7 (281.66 g, 97%). 1H NMR data identical with the data obtained earlier.

Workup

customA slightly exothermic reaction
customThe reaction was quenched by the addition of 10% aqueous NaOH (1.8 L) over a period of 20 min
customThe organic layer was separated
washwashed with brine (1 L)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-ddc1a2612aac4a20be68a368821b9254
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178552B2

Reaction notes

Loading…